Hydrochloric Acid → Methyl 3-amino-2,5-dichloro-4-methylbenzoate

HRID 34586Notes

Reaction equation

HRID 34586 reaction equation
[NH2:1][C:2]1[C:3]([Cl:13])=[C:4]([CH:8]=[C:9]([Cl:12])[C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].CO.Cl.[C:17](=O)([O-])[O-].[Na+].[Na+]>O>[NH2:1][C:2]1[C:3]([Cl:13])=[C:4]([CH:8]=[C:9]([Cl:12])[C:10]=1[CH3:11])[C:5]([O:7][CH3:17])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 10340Sodium CarbonateHCID 136574473-Amino-2,5-dichloro-4-methylbenzoic acid

Product 1

HCID 13657454Methyl 3-amino-2,5-dichloro-4-methylbenzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

30 g of 3-amino-2,5-dichloro-4-methylbenzoic acid are initially introduced into 140 ml of MeOH. HCl gas is now passed in for 20 minutes and the mixture is then boiled under reflux for a further 5 hours. After cooling, the mixture is poured into water and rendered alkaline with sodium carbonate. The ester which has precipitated is isolated and dried. Yield: 30.8 g, melting point: 53°-55°.

Workup

  1. customis now passed in for 20 minutes
  2. temperatureunder reflux for a further 5 hours
  3. temperatureAfter cooling
  4. customThe ester which has precipitated
  5. customis isolated
  6. customdried

Sources & evidence

ORD record
ord-2edbf5d5bd344535904fb4ffbf640a78
Source dataset
uspto-grants-1988_08
Patent number
US04762844

Reaction notes

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