Ammonia → 2-Naphthalenecarboxamide, 5,6-dihydro-7-(1H-imidazol-1-yl)-

HRID 1980548Notes

Reaction equation

HRID 1980548 reaction equation
[N:1]1([C:6]2[CH2:7][CH2:8][C:9]3[C:14]([CH:15]=2)=[CH:13][C:12]([C:16]([OH:18])=O)=[CH:11][CH:10]=3)[CH:5]=[CH:4][N:3]=[CH:2]1.[NH3:19]>CN(C=O)C>[N:1]1([C:6]2[CH2:7][CH2:8][C:9]3[C:14]([CH:15]=2)=[CH:13][C:12]([C:16](=[O:18])[NH2:19])=[CH:11][CH:10]=3)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 56009Rolafagrel

Product 1

HCID 30215672-Naphthalenecarboxamide, 5,6-dihydro-7-(1H-imidazol-1-yl)-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 1,2-dihydro-3-(1-imidazolyl)-6-carboxy-naphthalene (500 mg) in DMF (10 ml) SOCl2 (2 ml) was added. Cooling in an ice bath, NH3 was passed through the reaction mixture, with stirring, for 5 hours. The reaction mixture was allowed to stand for 12 hours. The ammonium salt was filtered off and Et2O was added giving a precipitate which was chromatographed on silica gel with CHCl3 :CH3OH:CH3COOH (45:5:2.5) as eluant; 350 mg of 1,2-dihydro-3-(1-imidazolyl)-6-carbamoyl-naphthalene were obtained.

Workup

  1. additionwas added
  2. temperatureCooling in an ice bath
  3. waitto stand for 12 hours
  4. filtrationThe ammonium salt was filtered off
  5. additionEt2O was added
  6. customgiving a precipitate which
  7. customwas chromatographed on silica gel with CHCl3 :CH3OH:CH3COOH (45:5:2.5) as eluant

Sources & evidence

ORD record
ord-ebb4d65296ac4506a6d20c993e91dadf
Source dataset
uspto-grants-1985_04
Patent number
US04510149

Reaction notes

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