Methyl 4-chloroanthranilate → HCID 19421832, compound

HRID 744116Notes

Reaction equation

HRID 744116 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10](Cl)=[O:11])[CH:6]=[CH:7][CH:8]=1.[NH2:13][C:14]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17]>ClCCl>[Cl:24][C:22]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:14]([NH:13][C:10](=[O:11])[CH2:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:23]=1

Participants

4

Reactant 2

HCID 80001Methyl 4-chloroanthranilateHCID 27332463-Methoxyphenylacetyl chloride

Product 1

HCID 19421832HCID 19421832, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Methoxyphenylacetyl chloride (1.11 g, 6 mmol) was added to methyl 2-amino-4-chlorobenzoate (0.93 g, 5 mmol) in dichloromethane (30 ml) and the solution stirred under reflux for 18 h. The oily residue remaining on evaporation of the solvent was triturated with diethyl ether to afford methyl 4-chloro-2-(3-methoxyphenyl)acetamidobenzoate as a colourless solid (1.51 g), m.p. 144°-146° C.

Workup

  1. temperatureunder reflux for 18 h
  2. customThe oily residue remaining on evaporation of the solvent
  3. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-2ee79c6bdc514d45b0e6b312f693d179
Source dataset
uspto-grants-1996_09
Patent number
US05559125

Reaction notes

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