Sodium Hydroxide → 2-(4-[1,4]Diazepan-1-yl-3-methoxy-phenyl)-6-hydroxy-3,4-dihydro-2H-isoquinolin-1-one

HRID 69470Notes

Reaction equation

HRID 69470 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:30][CH2:29][C:28]4[C:23](=[CH:24][CH:25]=[C:26]([O:31]C)[CH:27]=4)[C:22]3=[O:33])=[CH:17][C:16]=2[O:34][CH3:35])[CH2:10][CH2:9]1)=O)(C)(C)C.[OH-].[Na+]>Br>[N:11]1([C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:30][CH2:29][C:28]4[C:23](=[CH:24][CH:25]=[C:26]([OH:31])[CH:27]=4)[C:22]3=[O:33])=[CH:17][C:16]=2[O:34][CH3:35])[CH2:12][CH2:13][CH2:14][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 689888154-[2-Methoxy-4-(6-methoxy-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-phenyl]-[1,4]diazepane-1-carboxylic acid tert-butyl ester

Product 1

HCID 689904732-(4-[1,4]Diazepan-1-yl-3-methoxy-phenyl)-6-hydroxy-3,4-dihydro-2H-isoquinolin-1-one

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A solution of 4-[2-methoxy-4-(6-methoxy-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-phenyl]-[1,4]diazepane-1-carboxylic acid tert-butyl ester in 48% HBr (10 mL) was stirred for 48 h at 80° C. The mixture was neutralized with sodium hydroxide solution, extracted with dichloromethane, dried over magnesium sulfate and concentrated. In this way the product was obtained with molecular weight 367.45 (C21H25N3O3); MS (ESI): 368 (M+H+).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customIn this way the product was obtained with molecular weight 367.45 (C21H25N3O3)

Sources & evidence

ORD record
ord-90a4a93cc84242b9a6f49791be6e02e7
Source dataset
uspto-grants-2014_09
Patent number
US08822495B2

Reaction notes

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