Ammonia → 4H-Imidazo[4,5,1-ij]quinolin-2(1H)-one,5,6-dihydro-5-(propylamino)-, (5R)-

HRID 327459Notes

Reaction equation

HRID 327459 reaction equation
C([BH3-])#N.[Na+].[NH2:5][CH:6]1[CH2:15][C:14]2[C:9]3=[C:10]([NH:16][C:17](=[O:18])[N:8]3[CH2:7]1)[CH:11]=[CH:12][CH:13]=2.C[O-].[Na+].[CH:22](=O)[CH2:23][CH3:24].N>CO.C(Cl)(Cl)Cl>[CH2:22]([NH:5][CH:6]1[CH2:15][C:14]2[C:9]3=[C:10]([NH:16][C:17](=[O:18])[N:8]3[CH2:7]1)[CH:11]=[CH:12][CH:13]=2)[CH2:23][CH3:24]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 527PropanalHCID 5003444Sodium cyanoborohydrideHCID 10942334Sodium MethoxideHCID 159377665-Amino-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one

Product 1

HCID 112069974H-Imidazo[4,5,1-ij]quinolin-2(1H)-one,5,6-dihydro-5-(propylamino)-, (5R)-Yield 64%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

Sodium cyanoborohydride (0.17 g) was added in small portions over a 5-hour period to a stirred solution of 1.90 g (8.4 mmol) 5-amino-5,6-dihydro-4H-imidazo(4,5,1-ij)quinolin-2(1H)-one, 0.85 mL sodium methoxide and 1.5 g propionaldehyde in methanol (175 mL). Methanolic ammonia solution was added, and after 30 minutes, the solvent was evaporated. The residual oil was partitioned between ethyl acetate and water and the crude product obtained by evaporating the ethyl acetate was dissolved in chloroform and chromatographed on silica gel eluting with 2.5% methanol:chloroform to give 1.24 g (64% yield) of 5,6-dihydro-5-(propylamino)-4H-imidazo(4,5,1-ij)quinolin-2(1H)-one.

Workup

  1. customthe solvent was evaporated
  2. customThe residual oil was partitioned between ethyl acetate and water
  3. customthe crude product obtained
  4. customby evaporating the ethyl acetate
  5. dissolutionwas dissolved in chloroform
  6. customchromatographed on silica gel eluting with 2.5% methanol

Sources & evidence

ORD record
ord-f145658c946d4bb0b852c44394a0c964
Source dataset
uspto-grants-1993_12
Patent number
US05273975

Reaction notes

Loading…