Ammonium Chloride → HCID 9966080, compound

HRID 723381Notes

Reaction equation

HRID 723381 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:13]3[NH:12][CH:11]([C:14]4[CH:18]=[CH:17][S:16][CH:15]=4)[CH2:10][C:9](=[O:19])[C:8]=3[CH:7]=[CH:6][N:5]2[C:20]=1[CH3:21].[BH4-].[Na+].[Cl-].[NH4+]>CO>[OH:19][CH:9]1[C:8]2[CH:7]=[CH:6][N:5]3[C:20]([CH3:21])=[C:2]([CH3:1])[N:3]=[C:4]3[C:13]=2[NH:12][CH:11]([C:14]2[CH:18]=[CH:17][S:16][CH:15]=2)[CH2:10]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 21873976HCID 21873976, compound

Product 1

HCID 9966080HCID 9966080, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1 g of 2,3-dimethyl-9-(3-thienyl)-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one, suspended in 10 ml of methanol, is treated with 500 mg of sodium borohydride, the solvent is stripped off in vacuo after stirring at room temperature for 1 hour, the yellowish residue is treated with saturated aqueous ammonium chloride solution (100 ml) and the mixture is extracted three times with methylene chloride. The combined organic phases are washed with a little water, dried over sodium sulfate and the solvent is stripped off in vacuo. The remaining solid residue is stirred with a little (15 ml) diethyl ether and then filtered off. 0.88 g of the title compound of m.p. 192–94° C. (diethyl ether) is obtained.

Workup

  1. extractionthe mixture is extracted three times with methylene chloride
  2. washThe combined organic phases are washed with a little water
  3. dry with materialdried over sodium sulfate
  4. stirringThe remaining solid residue is stirred with a little (15 ml) diethyl ether
  5. filtrationfiltered off

Sources & evidence

ORD record
ord-05185e17c0d249ee9ee205c689dd2cbe
Source dataset
uspto-grants-2006_11
Patent number
US07141567B2

Reaction notes

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