Methanol → Methyl 2-(4-chlorophenyl)-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)acetate

HRID 1161250Notes

Reaction equation

HRID 1161250 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7]O[C:9]2=[O:14])([O-:3])=[O:2].CO.C(N(CC)CC)C.Cl.[NH2:25][CH:26]([C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=1)[C:27]([O:29][CH3:30])=[O:28]>>[Cl:37][C:34]1[CH:33]=[CH:32][C:31]([CH:26]([N:25]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][CH:12]=[CH:13][C:4]=3[N+:1]([O-:3])=[O:2])[C:9]2=[O:14])[C:27]([O:29][CH3:30])=[O:28])=[CH:36][CH:35]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 100127605-nitro-1H-isochromen-1-oneHCID 12803949Methyl 2-amino-2-(4-chlorophenyl)acetate hydrochloride

Product 1

HCID 58973969Methyl 2-(4-chlorophenyl)-2-(5-nitro-1-oxoisoquinolin-2(1H)-yl)acetate

Conditions

Temperature
50 °C

Procedure

A round bottom flask was charged with 5-nitro-isochromen-1-one (2.5 g, 0.013 mol), methanol (40 mL, 1 mol), triethylamine (4 mL, 0.03 mol) and methyl 2-amino-2-(4-chlorophenyl)acetate hydrochloride (4.0 g, 0.017 mol) and the reaction heated at 50° C. for 4 hours. The solvent was removed and the residue purified by flash chromatography (40 g silica gel, 0-10% MOH/DCM) to yield the product as a yellow solid. MS m/z=373.3 (M+H).

Workup

  1. customThe solvent was removed
  2. customthe residue purified by flash chromatography (40 g silica gel, 0-10% MOH/DCM)

Sources & evidence

ORD record
ord-702adf24d1954e118f899294b8cfd5fd
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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