4,4-Dimethyl-1,3(2H,4H)-isoquinolinedione → HCID 21428623, compound

HRID 437586Notes

Reaction equation

HRID 437586 reaction equation
[CH3:1][C:2]1([CH3:19])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[N:4]([CH2:13][CH2:14][CH2:15][C:16]#[N:17])[C:3]1=[O:18].CC1(C)C2C(=CC=CC=2)C(=O)NC1=O>N.[Ni].O>[CH3:1][C:2]1([CH3:19])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[N:4]([CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])[C:3]1=[O:18]

Participants

6

Reactant 2

HCID 3380304,4-Dimethyl-1,3(2H,4H)-isoquinolinedioneHCID 21428636HCID 21428636, compound

Product 1

HCID 21428623HCID 21428623, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 962WaterSolvent

Procedure

2.56 gm of 4,4-dimethyl-2-(3-cyano-propyl)-1,2,3,4-tetrahydro-isoquinoline-1,3-dione prepared from 4,4-dimethyl-1,2,3,4-tetrahydro-isoquinoline-1,3-dione and 4-chlorobutyric acid nitrile) were dissolved in 50 ml of methanolic ammonia, and the solution was hydrogenated in the presence of 1 gm of Raney nickel at 50° C and 5 atmospheres pressure for 2 hours. The reaction mixture was then diluted with water, acidified and extracted with chloroform. The aqueous phase was made alkaline, extracted with chloroform, and the chloroform extract was evaporated. The residue was used as the starting compound in the following step without purification.

Workup

  1. extractionextracted with chloroform
  2. extractionextracted with chloroform
  3. extractionthe chloroform extract
  4. customwas evaporated
  5. customThe residue was used as the starting compound in the following step without purification

Sources & evidence

ORD record
ord-444d5c16d8bd4266963519dd43fa2370
Source dataset
uspto-grants-1977_06
Patent number
US04031219

Reaction notes

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