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

HRID 745980Notes

Reaction equation

HRID 745980 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 4 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

Sources & evidence

ORD record
ord-01c39f10fd8e405e91d60c7f4b803f7a
Source dataset
uspto-grants-1986_07
Patent number
US04602022

Reaction notes

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