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Acetic Acid → Methyl 2-{2-[(4-methoxyphenyl)amino]ethyl}-1-oxo-1,2-dihydroisoquinoline-7-carboxylate

HRID 1616153
Notes
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Reaction equation

HRID 1616153 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=2)[CH:5]=[CH:4][N:3]1[CH2:16][CH:17]=O.[CH3:19][O:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO.O>[CH3:19][O:20][C:21]1[CH:27]=[CH:26][C:24]([NH:25][CH2:17][CH2:16][N:3]2[CH:4]=[CH:5][C:6]3[C:11](=[CH:10][C:9]([C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:7]=3)[C:2]2=[O:1])=[CH:23][CH:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7732P-AnisidineHCID 5003444Sodium cyanoborohydrideHCID 86664205Methyl 1-oxo-2-(2-oxoethyl)-1,2-dihydroisoquinoline-7-carboxylate

Product 1

HCID 67282872Methyl 2-{2-[(4-methoxyphenyl)amino]ethyl}-1-oxo-1,2-dihydroisoquinoline-7-carboxylateYield 83.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of methyl 1-oxo-2-(2-oxoethyl)-1,2-dihydroisoquinoline-7-carboxylate (0.10 g, 0.41 mmol) and 4-methoxyaniline (65 mg, 0.53 mmol) in methanol (2 mL) was stirred at rt for 30 mins. Then acetic acid (2.3 μL, 0.04 mmol) and sodium cyanoborohydride (64 mg, 1.0 mmol) was added and the reaction mixture was stirred at rt overnight. The mixture was diluted with water and extracted with DCM (2×). The combined organic phases were then washed with water, and brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash silica gel chromatography (20% to 70% EtOAc/hexanes) to afford methyl 2-{2-[(4-methoxyphenyl)amino]ethyl}-1-oxo-1,2-dihydroisoquinoline-7-carboxylate (0.12 g, 83%). LC-MS: (FA) ES+ 353.

Workup

  1. extractionextracted with DCM (2×)
  2. washThe combined organic phases were then washed with water, and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash silica gel chromatography (20% to 70% EtOAc/hexanes)

Sources & evidence

ORD record
ord-af57a4746c3946ecabb98b0a0c0956c1
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08765773B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes