Ammonium Chloride → HCID 69291707, compound

HRID 584850Notes

Reaction equation

HRID 584850 reaction equation
C([O:4][C:5]1[C:14]2[CH:13]=[CH:12][N:11]3[C:15]([CH3:19])=[C:16]([CH3:18])[N:17]=[C:10]3[C:9]=2[N:8]([C:20](=[O:22])[CH3:21])[CH:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=1)(=O)C.[BH4-].[Na+].[Cl-].[NH4+]>CO.ClCCl>[C:20]([N:8]1[C:9]2[C:10]3=[N:17][C:16]([CH3:18])=[C:15]([CH3:19])[N:11]3[CH:12]=[CH:13][C:14]=2[C@@H:5]([OH:4])[CH2:6][C@H:7]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:22])[CH3:21]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 10150418HCID 10150418, compound

Product 1

HCID 69291707HCID 69291707, compoundYield 75.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

12.2 g (32.5 mmol) of rac-7-acetoxy-10-acetyl-2,3-dimethyl-9-phenyl-9,10-dihydroimidazo[1,2-h][1,7]naphthyridine are dissolved in 50 ml of methanol and 10 ml of dichloromethane. 5.0 g (132 mmol) of sodium borohydride are then introduced at 0° C. over a period of 2 h. After 3 h, 30 ml of saturated ammonium chloride solution are added. The reaction mixture is extracted with dichloromethane, and the organic phase is dried over magnesium sulfate and evaporated. The residue is crystallized using diethyl ether. 8.2 g (75%) of the title compound are isolated as a colorless solid (m.p. 217° C.).

Workup

  1. extractionThe reaction mixture is extracted with dichloromethane
  2. dry with materialthe organic phase is dried over magnesium sulfate
  3. customevaporated
  4. customThe residue is crystallized

Sources & evidence

ORD record
ord-b0bc6735faf44887b6896bfe30d5dd0b
Source dataset
uspto-grants-2005_08
Patent number
US06927292B2

Reaction notes

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