Ammonium Hydroxide → HCID 22175497, compound

HRID 1797678Notes

Reaction equation

HRID 1797678 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:6]([C:17]#[N:18])=[C:5]2[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[OH-].[NH4+].[H][H]>[Co].O1CCCC1>[NH2:18][CH2:17][C:6]1[N:7]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:8](=[O:12])[C:9]2[C:4]([C:5]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[CH:3][C:2]([Br:1])=[CH:11][CH:10]=2

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 22175379HCID 22175379, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22175497HCID 22175497, compoundYield 91.5%

Reagents, catalysts & solvents 2

HCID 104730CobaltCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 6-bromo-2-isobutyl-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carbonitrile (16.0 g), sponge cobalt (manufactured by Kawaken Fine Chemicals Co., Ltd.; trademark: ODHT-60) (4 ml), 25% ammonium hydroxide (2 ml) and tetrahydrofuran. (80 ml) was stirred at 60° C. at a 1 MPa hydrogen pressure for 4 h and the catalyst was filtered off. The solvent was evaporated and acetonitrile (48 ml) was added to the residue. The mixture was heated to about 70° C. The obtained solution was cooled to 25° C. to give crystals, and water (80 ml) was added dropwise. The obtained mixture was cooled to around 5° C. and the mixture was stirred for 1 h. The precipitated crystals were collected by filtration to give the title compound (14.8 g, yield 91.4%).

Workup

  1. filtrationthe catalyst was filtered off
  2. customThe solvent was evaporated
  3. additionacetonitrile (48 ml) was added to the residue
  4. temperatureThe obtained solution was cooled to 25° C.
  5. customto give crystals, and water (80 ml)
  6. additionwas added dropwise
  7. temperatureThe obtained mixture was cooled to around 5° C.
  8. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-8d3b7367a23b48bc9da5fa8a63899259
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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