Hydrochloric Acid → 3-Amino-2,5-dichloro-4-methylbenzoic acid

HRID 34585Notes

Reaction equation

HRID 34585 reaction equation
[Cl:1][C:2]1[C:10]([N+:11]([O-])=O)=[C:9]([CH3:14])[C:8]([Cl:15])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[O-]S(S([O-])=O)=O.[Na+].[Na+].Cl.C([O-])([O-])=O.[Na+].[Na+]>COCCO.O>[NH2:11][C:10]1[C:2]([Cl:1])=[C:3]([CH:7]=[C:8]([Cl:15])[C:9]=1[CH3:14])[C:4]([OH:6])=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 24489Sodium DithioniteHCID 136574462,5-Dichloro-4-methyl-3-nitrobenzoic acid

Product 1

HCID 136574473-Amino-2,5-dichloro-4-methylbenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80192-MethoxyethanolSolvent

Procedure

43 g of 2,5-dichloro-4-methyl-3-nitrobenzoic acid and 108.8 g of Na2S2O4 are boiled in a mixture of 340 ml of glycol monomethyl ether and 340 ml of water for 3 hours. 480 ml of 1/2-concentrated HCl are added to the still warm solution and the mixture is then boiled up once again. After cooling to room temperature, the mixture is poured into 1 l of ice-water and the strongly acid solution is buffered with Na2CO3 (pH 5). The solid which has precipitated is isolated and dried. Melting point: 218°-21°, yield: 32.5 g.

Workup

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

Sources & evidence

ORD record
ord-71c923af91b64034a7eea64cf3aa16cc
Source dataset
uspto-grants-1988_08
Patent number
US04762844

Reaction notes

Loading…