Hydrochloric Acid → 3-Amino-2-chloro-5-fluoro-4-methylbenzoic acid

HRID 34578

Reaction equation

HRID 34578 reaction equation
[Cl:1][C:2]1[C:10]([N+:11]([O-])=O)=[C:9]([CH3:14])[C:8]([F:15])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[O-]S(S([O-])=O)=O.[Na+].[Na+].Cl>COCCO.O>[NH2:11][C:10]1[C:2]([Cl:1])=[C:3]([CH:7]=[C:8]([F:15])[C:9]=1[CH3:14])[C:4]([OH:6])=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24489Sodium DithioniteHCID 136574392-Chloro-5-fluoro-4-methyl-3-nitro-benzoic acid

Product 1

HCID 136574403-Amino-2-chloro-5-fluoro-4-methylbenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 80192-MethoxyethanolSolvent

Procedure

18.5 g of 2-chloro-5-fluoro-4-methyl-3-nitro-benzoic acid and 51.5 g of Na2S2O4 are boiled in a mixture of 160 ml of glycol monomethyl ether and 160 g of water for 3 hours. 230 ml of 1/2-concentrated HCl are added to the still warm solution. The mixture is boiled up once more, cooled and poured into 560 ml of water. The solid which has precipitated is isolated and dried. Yield: 12.4 g, melting point: 182°-84°.

Workup

  1. temperaturecooled
  2. customThe solid which has precipitated
  3. customis isolated
  4. customdried

Sources & evidence

ORD record
ord-59d9ecf81f1c4d51bdbef875b42cf00b
Source dataset
uspto-grants-1988_08
Patent number
US04762844

Linked notes

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