Methylamine ethanol → 7-Benzyloxy-3-hydroxymethyl-2-methyl-4-(5-methyl-chroman-6-yl)-2H-isoquinolin-1-one

HRID 572490Notes

Reaction equation

HRID 572490 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([C:29]3[C:30]([CH3:39])=[C:31]4[C:36](=[CH:37][CH:38]=3)[O:35][CH2:34][CH2:33][CH2:32]4)=[C:14]([C:20](C)(C)[O:21][SiH2]C(C)(C)C)[O:15][C:16]2=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:40][NH2:41].CCO>>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([C:29]3[C:30]([CH3:39])=[C:31]4[C:36](=[CH:37][CH:38]=3)[O:35][CH2:34][CH2:33][CH2:32]4)=[C:14]([CH2:20][OH:21])[N:41]([CH3:40])[C:16]2=[O:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 22028356Methylamine ethanolHCID 178421998HCID 178421998, compound

Product 1

HCID 682957767-Benzyloxy-3-hydroxymethyl-2-methyl-4-(5-methyl-chroman-6-yl)-2H-isoquinolin-1-oneYield 86%

Conditions

Temperature
80 °C

Procedure

The mixture of 7-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxymethyl)-4-(5-methyl-chroman-6-yl)-isochromen-1-one (5.0 g, 9.21 mmol) and CH3NH2/EtOH (10 mL) was stirred at 80° C. for 1 hour. The solvent was removed in vacuo and the resulting mixture was acidified by HCl-EA solution to pH 1-2. The mixture was diluted with water and extracted with EA (3*100 mL) and dried over sodium sulfate and concentrated to dryness. The residue was purified by chromatography column on silica gel to afford title product (3.5 g, 86%).

Workup

  1. customThe solvent was removed in vacuo
  2. additionThe mixture was diluted with water
  3. extractionextracted with EA (3*100 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by chromatography column on silica gel

Sources & evidence

ORD record
ord-db09664cc2a54b5b89860815e2825e93
Source dataset
uspto-grants-2015_05
Patent number
US09029391B2

Reaction notes

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