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

HRID 1971776Notes

Reaction equation

C(#N)C.[Cl:4]N1C(=O)CCC1=O.[NH2:12][C:13]1[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][C:14]=1[O:24][CH3:25]>CCCCCCC.C(OCC)(=O)C>[NH2:12][C:13]1[C:14]([O:24][CH3:25])=[CH:15][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:22][C:23]=1[Cl:4]

Participants

Conditions

Temperature: 60 °C

Procedure

After adding acetonitrile (170 mL) and N-chlorosuccinimide (13.4 g, 100 mmol) to ethyl 4-amino-3-methoxybenzoate (17.8 g, 91.2 mmol) in that order, the mixture was stirred at 60° C. for 2 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 (mixture of n-heptane and ethyl acetate: n-heptane/ethyl acetate=8/1 then 4/1) to obtain the title compound (15.8 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 (
additionmixture of n-heptane and ethyl acetate

Sources & evidence

ORD record: ord-9c3ca67a2e00410685b0dceb0dff1fdd
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431603B2

Reaction notes

Loading…