Hydrochloric Acid → 3-Methylsulfonyl-4-chloro-5-aminobenzoic acid

HRID 1606615Notes

Reaction equation

HRID 1606615 reaction equation
[Cl-].[NH4+].Cl.[CH3:4][S:5]([C:8]1[CH:9]=[C:10]([CH:14]=[C:15]([N+:18]([O-])=O)[C:16]=1[Cl:17])[C:11]([OH:13])=[O:12])(=[O:7])=[O:6]>[Fe].O>[ClH:17].[CH3:4][S:5]([C:8]1[CH:9]=[C:10]([CH:14]=[C:15]([NH2:18])[C:16]=1[Cl:17])[C:11]([OH:13])=[O:12])(=[O:7])=[O:6]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 122745753-Methylsulfonyl-4-chloro-5-nitrobenzoic acid

Product 2

HCID 313Hydrochloric AcidHCID 189525243-Methylsulfonyl-4-chloro-5-aminobenzoic acidYield 123.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A vigorously stirred mixture of iron powder (9.2 g.), ammonium chloride (880 mg.) water (27 ml.) and concentrated hydrochloric acid (0.1 ml.) is heated on a steam bath while 3-methylsulfonyl-4-chloro-5-nitrobenzoic acid (7.8 g.) is added in small portions during a one hour period. The reaction mixture is heated on a steam bath for 18 hours, cooled and filtered. The filter cake is suspended in water (75 ml.), basified with 10N sodium hydroxide, warmed to 50° C. and filtered. Acidification of the filtrate with hydrochloric acid gives pure 3-methylsulfonyl-4-chloro-5-aminobenzoic acid (4.3 g.; 62%) which melts at 277.5° C.

Workup

  1. additionis added in small portions during a one hour period
  2. temperatureThe reaction mixture is heated on a steam bath for 18 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. filtrationfiltered

Sources & evidence

ORD record
ord-5920c10d7fd442efbe4d9a174435e64f
Source dataset
uspto-grants-1976_04
Patent number
US03953476

Reaction notes

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