2-Amino-N-isopropylacetamide → 2-[3-(3-chlorophenyl)-7-methoxy-1-oxo-1H-isoquinolin-2-yl]-N-isopropylacetamide

HRID 602279Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2O[C:10](=[O:20])[C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[C:13]([O:18][CH3:19])[CH:12]=3)[CH:5]=[CH:6][CH:7]=1.[NH2:21][CH2:22][C:23]([NH:25][CH:26]([CH3:28])[CH3:27])=[O:24]>CCO>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:21]([CH2:22][C:23]([NH:25][CH:26]([CH3:28])[CH3:27])=[O:24])[C:10](=[O:20])[C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[C:13]([O:18][CH3:19])[CH:12]=3)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

In an open, 50 mL two-necked round bottom flask, a neat mixture of compound 3-(3-chlorophenyl)-7-methoxyisochromen-1-one (1.00 g, 3.49 mmol) and 2-amino-N-isopropylacetamide (INTERMEDIATE I.1) (2.02 g, 17.4 mmol, 5 eq) was heated to 120° C. under argon for 3 days, adding absolute EtOH in aliquots (2 mL) daily to loosen up the reaction mixture. The residue was purified by chromatography on silica gel with ethyl acetate:hexane (1:3, v/v) as eluent to give 2-[3-(3-chlorophenyl)-7-methoxy-1-oxo-1H-isoquinolin-2-yl]-N-isopropylacetamide (0.985 g, 2.56 mmol, 73%) as a white solid.

Workup

customThe residue was purified by chromatography on silica gel with ethyl acetate:hexane (1:3

Sources & evidence

ORD record: ord-f00bf45ec205493eb2b475ee5edf1332
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906504B2

Reaction notes

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