Ammonium Chloride → HCID 69291707, compound

HRID 2249706Notes

Reaction equation

HRID 2249706 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 using dichloromethane, and the organic phase is dried over magnesium sulphate 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
  2. dry with materialthe organic phase is dried over magnesium sulphate
  3. customevaporated
  4. customThe residue is crystallized

Sources & evidence

ORD record
ord-8307c91a6481413ab65a939c5488e3e6
Source dataset
uspto-grants-2008_01
Patent number
US07314935B2

Reaction notes

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