Sodium borohydride → 7-(4-Hydroxy-pentyloxy)-1,3-dihydro-imidazo[4,5-b]quinolin-2-one

HRID 867494Notes

Reaction equation

HRID 867494 reaction equation
[BH4-].[Na+].[O:3]=[C:4]([CH3:23])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:18]=[CH:17][C:16]2[N:15]=[C:14]3[NH:19][C:20](=[O:22])[NH:21][C:13]3=[CH:12][C:11]=2[CH:10]=1>CO.CN(C)C=O>[OH:3][CH:4]([CH3:23])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:18]=[CH:17][C:16]2[N:15]=[C:14]3[NH:19][C:20](=[O:22])[NH:21][C:13]3=[CH:12][C:11]=2[CH:10]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 142810207-(4-Oxo-pentyloxy)-1,3-dihydro-imidazo[4,5-b]quinolin-2-one

Product 1

HCID 142810417-(4-Hydroxy-pentyloxy)-1,3-dihydro-imidazo[4,5-b]quinolin-2-oneYield 86%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium borohydride (1.00 g, 26 mmol) was added portionwise to a stirred suspension of 1,3-dihydro-7-(4-oxopentoxy)-2H-imidazo[4,5-b]quinolin-2-one (3.70 g, 13 mmol) in methanol (85 mL) and dimethylformamide (85 mL). The mixture was stirred at room temperature for 3 hours and then the solvent removed in vacuo. The residual oil was triturated with water (50 mL) and the solid material filtered off, washed with water and dried in air. Crystallization from aqueous dimethylformamide followed by trituration with methanol afforded 1,3-dihydro-7-(4-hydroxypentoxy)-2H-imidazo[4,5-b]-quinolin-2-one (3.20 g, 86%), m.p. 301°-303° C.

Workup

  1. customthe solvent removed in vacuo
  2. customThe residual oil was triturated with water (50 mL)
  3. filtrationthe solid material filtered off
  4. washwashed with water
  5. customdried in air
  6. customCrystallization from aqueous dimethylformamide

Sources & evidence

ORD record
ord-aadac411cc0f49a6bccceb13c801e3ff
Source dataset
uspto-grants-1988_10
Patent number
US04775674

Reaction notes

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