5-Chloro-2,4-dimethoxybenzoyl chloride → HCID 18687450, compound

HRID 1872735Notes

Reaction equation

HRID 1872735 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][N:5]([CH3:11])[CH2:6]2.[Cl:12][C:13]1[C:14]([O:24][CH3:25])=[CH:15][C:16]([O:22][CH3:23])=[C:17]([CH:21]=1)[C:18](Cl)=[O:19]>ClCCl>[ClH:12].[CH3:11][N:5]1[CH2:4][C:3]2[C:7](=[CH:8][CH:9]=[CH:10][C:2]=2[NH:1][C:18](=[O:19])[C:17]2[CH:21]=[C:13]([Cl:12])[C:14]([O:24][CH3:25])=[CH:15][C:16]=2[O:22][CH3:23])[CH2:6]1

Participants

4

Reactant 2

HCID 186874425-Chloro-2,4-dimethoxybenzoyl chlorideHCID 21138365HCID 21138365, compound

Product 1

HCID 18687450HCID 18687450, compoundYield 19.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of freshly prepared 4-amino-2,3-dihydro-2-methyl-1H-isoindole (400 mg, 3.0 mmol) in dry ethyl acethate (40 ml) under argon was treated dropwise with a solution of 5-chloro-2,4-dimethoxybenzoyl chloride (700 mg, 3.0 mmol) in a mixture of ethyl acethate (10 ml) and dichloromethane (10 ml). The reaction was stirred at room temperature for 6h and then concentrated in vacuo. The residue was triturated with diethyl ether/ethyl acethate and then crystallised twice from methanol/diethyl ether to give the title compound as a pale grey solid (0.11 g).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was triturated with diethyl ether/ethyl acethate
  3. customcrystallised twice from methanol/diethyl ether

Sources & evidence

ORD record
ord-ce8fd4cc5047409dbfade900572945fa
Source dataset
uspto-grants-2000_08
Patent number
US06110934

Reaction notes

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