Claims
- 1. The process of making a compound of the formula (1) ##STR8## wherein Y and Z are independently hydrogen, halogen, alkyl, alkoxy, trifluoromethyl, hydroxy, alkanoyloxy, or alkanoylamino;
- X is F, Cl, or Br; and
- R is hydrogen, alkyl, cycloalkyl, or aryl-alkyl; from a compound of the formula (2) ##STR9## wherein Y, Z and R have the meanings given above, comprising: (a) reacting a compound of formula (2) with a sulfonating agent which directly substitutes a sulfonic group --SO.sub.2 X onto the pendant phenyl ring of formula (2); and then
- (b) oxidizing the product of step (a) to form the compound of formula (1);
- wherein the alkyl, alkoxy, alkanoyloxy, alkanoylamino, and cycloalkyl groups and the alkyl moiety of aryl-alkyl can each contain up to 10 carbon atoms, and the aryl moieties of aryl-alkyl are hydrocarbyl groups containing up to 10 carbon atoms.
- 2. The process of claim 1 wherein
- Y is halogen or trifluoromethyl; and
- Z and R are hydrogen.
- 3. The process of claim 2 wherein Y is in the para-position.
- 4. The process of claim 3 wherein the --SO.sub.2 X group is in the meta-position.
- 5. The process of claim 4 wherein Y is chloro.
- 6. The process of claim 5 wherein the sulfonating agent is chlorosulfonic acid, bromosulfonic acid, or fluorosulfonic acid.
- 7. The process of making a compound of the formula (3) ##STR10## comprising (a) reacting a compound of the formula (4) ##STR11## with an acid of the formula HSO.sub.3 X wherein X is Cl, Br, or F, thereby substituting a group --SO.sub.2 X onto the meta-position of the pendant phenyl ring of formula (4); and then
- (b) oxidizing the product of step (a) to form the 3-hydroxy derivative thereof; and
- (c) reacting the product of either step (a) or step (b) with a basic nitrogen compound to convert the --SO.sub.2 X group to a --SO.sub.2 NH.sub.2 group.
- 8. The process of claim 7 wherein the basic nitrogen compound is ammonia or ammonium hydroxide.
Parent Case Info
This application is a continuation of application Ser. No. 202,806 filed Oct. 13, 1980 abandoned.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
3055904 |
Graf et al. |
Sep 1962 |
|
Non-Patent Literature Citations (2)
Entry |
Schmidt et al., Chem. Ber., vol. 103, pp. 3783-3790, (1970). |
Elderfield, Heterocyclic Compounds, vol. 3, (John Wiley, N.Y., 1952), p. 285. |
Continuations (1)
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Number |
Date |
Country |
Parent |
202806 |
Oct 1980 |
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