N-methyl-2-pyrrolidone → HCID 20242569, compound

HRID 483141Notes

Reaction equation

HRID 483141 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][C:10](=[O:18])[NH:9]2)=[CH:4][CH:3]=1.[CH3:19][N:20]1CCCC1=O>C(N)CN>[C:19]([C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][C:10](=[O:18])[NH:9]2)=[CH:4][CH:3]=1)#[N:20]

Participants

4

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 2818273HCID 2818273, compound

Product 1

HCID 20242569HCID 20242569, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 3301EthylenediamineSolvent

Procedure

A solution of 1-(4-bromophenyl)-1,4-dihydroisoquinol-3-one (15.1 g, 50 mmol) and cuprous cyanide (8.95 g, 100 mmol) in N-methylpyrrolidinone (150 ml) was heated under reflux under a nitrogen atmosphere for 2 h. The solution was cooled and diluted with 10% aqueous ethylenediamine solution (1000 ml), then extracted with ethyl acetate (4×250 ml). The combined extracts were washed with water (4×250 ml) and brine (250 ml), then dried (MgSO4) and evaporated to dryness to leave a pale brown solid which was crystallised from ethyl acetate to give the title compound (8.43 g, 68%), m.p. 165°-168° C. (ethanol).

Workup

  1. temperatureunder reflux under a nitrogen atmosphere for 2 h
  2. temperatureThe solution was cooled
  3. extractionextracted with ethyl acetate (4×250 ml)
  4. washThe combined extracts were washed with water (4×250 ml) and brine (250 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated to dryness
  7. customto leave a pale brown solid which
  8. customwas crystallised from ethyl acetate

Sources & evidence

ORD record
ord-d5214a54b4714c4d97ccd728ad4d9c4c
Source dataset
uspto-grants-1986_03
Patent number
US04578393

Reaction notes

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