Methanol → HCID 68472645, compound

HRID 387650Notes

Reaction equation

HRID 387650 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:22]([O-:24])=[O:23])[C:7]2[CH2:8][CH2:9][N:10]([CH:15]([CH2:19][CH2:20][CH3:21])[CH2:16][CH2:17][CH3:18])[C:11](=[O:14])[C:12]=2[CH:13]=1)([O-])=O.[H][H].[CH3:27]O>[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([C:22]([O:24][CH3:27])=[O:23])[C:7]2[CH2:8][CH2:9][N:10]([CH:15]([CH2:19][CH2:20][CH3:21])[CH2:16][CH2:17][CH3:18])[C:11](=[O:14])[C:12]=2[CH:13]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 68470607HCID 68470607, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68472645HCID 68472645, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

8.6 g of 7-nitro-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate, 10 cm3 of methanol and 28 mg of 10% (dry basis) palladium-on-carbon are stirred under 2 bar of hydrogen in an autoclave for 2 h 20 min at a temperature of 25° C. The catalyst is filtered through a Celite 545 pellet and washed with 2 lots of 100 cm3 of methanol. The filtrate is then concentrated under reduced pressure (5 kPa). 7.7 g of methyl 7-amino-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate are obtained in the form of a light green powder.

Workup

  1. filtrationThe catalyst is filtered through a Celite 545 pellet
  2. washwashed with 2 lots of 100 cm3 of methanol
  3. concentrationThe filtrate is then concentrated under reduced pressure (5 kPa)

Sources & evidence

ORD record
ord-3661139e0ae44ce4858622b0aa76347f
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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