Hydrochloric Acid → Methyl 2-[3-(isobutyrylamino)benzyl]-1-oxo-1,2-dihydroisoquinoline-7-carboxylate

HRID 1616170Notes

Reaction equation

HRID 1616170 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[CH2:5][N:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][C:10]([C:16]([O:18][CH3:19])=[O:17])=[CH:11][CH:12]=2)[C:7]1=[O:20].Cl.C(N(CC)CC)C.[CH3:32][CH:33]([CH3:37])[C:34](Cl)=[O:35]>C(Cl)Cl>[C:34]([NH:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[CH2:5][N:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][C:10]([C:16]([O:18][CH3:19])=[O:17])=[CH:11][CH:12]=2)[C:7]1=[O:20])(=[O:35])[CH:33]([CH3:37])[CH3:32]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 67282939Methyl 2-(3-aminobenzyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate

Product 1

HCID 67282403Methyl 2-[3-(isobutyrylamino)benzyl]-1-oxo-1,2-dihydroisoquinoline-7-carboxylateYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-(3-aminobenzyl)-1-oxo-1,2-dihydroisoquinoline-7-carboxylate.HCl (0.15 g, 0.44 mmol) dissolved in methylene chloride (5 mL) was added triethylamine (0.30 mL, 2.2 mmol) and 2-methylpropanoyl chloride (0.09 mL, 0.87 mmol). The reaction mixture was stirred at rt for 2 h. The mixture was then concentrated to dryness and the residue was purified by flash silica gel chromatography (0% to 5% EtOAc/DCM) to afford methyl 2-[3-(isobutyrylamino)benzyl]-1-oxo-1,2-dihydroisoquinoline-7-carboxylate (0.15 g, 88%). LC-MS: (FA) ES+ 379.

Workup

  1. concentrationThe mixture was then concentrated to dryness
  2. customthe residue was purified by flash silica gel chromatography (0% to 5% EtOAc/DCM)

Sources & evidence

ORD record
ord-0b85db60384545a691f588ee143b3798
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

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