Acetonitrile → Ethyl 4-amino-3-chloro-5-methoxybenzoate

HRID 41239Notes

Reaction equation

[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[O:13][CH3:14].C(#N)C.[Cl:18]N1C(=O)CCC1=O>CCCCCCC.C(OCC)(=O)C>[NH2:1][C:2]1[C:3]([O:13][CH3:14])=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][C:12]=1[Cl:18]

Participants

Conditions

Temperature: 60 °C

Procedure

To ethyl 4-amino-3-methoxybenzoate (17.8 g, 91.2 mmol), were added acetonitrile (170 mL) and N-chlorosuccinimide (13.4 g, 100 mmol) in this order, and the mixture was stirred at 60° C. for two hours. The mixture was returned to room temperature, and the solvent in the mixture was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate:n-heptane/ethyl acetate=8/1 then 4/1) to obtain the title compound (158 g, 68.8 mmol).

Workup

customwas returned to room temperature
distillationthe solvent in the mixture was distilled off under reduced pressure
customThe residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate

Sources & evidence

ORD record: ord-b8c786945fd84eac843c3a1a2c584a5f
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530504B2

Reaction notes

Loading…