Hydrochloric Acid → HCID 22750118, compound

HRID 2164052Notes

Reaction equation

HRID 2164052 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1([CH3:37])[C:13]2[C:8](=[CH:9][C:10]([O:16][CH3:17])=[C:11]([O:14][CH3:15])[CH:12]=2)[C:7](=[O:18])[N:6]([CH2:19][CH2:20][CH2:21][N:22]([CH3:35])[CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[CH:26]=2)[C:5]1=[O:36].Cl>O1CCOCC1.O>[OH:36][CH:5]1[C:4]([CH3:37])([CH3:3])[C:13]2[C:8](=[CH:9][C:10]([O:16][CH3:17])=[C:11]([O:14][CH3:15])[CH:12]=2)[C:7](=[O:18])[N:6]1[CH2:19][CH2:20][CH2:21][N:22]([CH3:35])[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[CH:26]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 14350344HCID 14350344, compound

Product 1

HCID 22750118HCID 22750118, compoundYield 81.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

0.49 gm (13.0 millimols) of sodium borohydride were added at 0° C. to a solution of 4.0 gm (8.2 millimols) of 1-[4,4-dimethyl-6,7-dimethoxy-1,3-dioxo-(2H,4H)-isoquinolin-2-yl]-3-[N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino]-propane in a mixture of 100 ml of dioxane and 20 ml of water. The mixture was stirred at room temperature for 8 hours and subsequently admixed with 100 ml of 2 N hydrochloric acid. After extraction with chloroform, the organic extract was dried over sodium sulfate and evaporated in vacuo, leaving as a residue 3.25 gm (80% of theory) of 1-[3-hydroxy-4,4-dimethyl-6,7-dimethoxy-3,4-dihydro-2H-isoquinolin-1-one-2-yl]-3-[N-methyl-N-(2-(3,4-dimethoxy-phenyl)-ethyl)-amino]-propane.

Workup

  1. extractionAfter extraction with chloroform
  2. extractionthe organic extract
  3. dry with materialwas dried over sodium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-bef5f3bba310493d88095dd800a76568
Source dataset
uspto-grants-1979_01
Patent number
US04137318

Reaction notes

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