Ammonium Chloride → HCID 18923211, compound

HRID 1290162Notes

Reaction equation

HRID 1290162 reaction equation
[Cl:1][C:2]1[C:19]([N:20]2[CH2:24][CH2:23][CH2:22][C:21]2=O)=[CH:18][CH:17]=[C:16]([Cl:26])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([CH:12]=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+]>O1CCCC1>[Cl:1][C:2]1[C:19]([N:20]2[CH2:21][CH2:22][CH2:23][CH2:24]2)=[CH:18][CH:17]=[C:16]([Cl:26])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([CH:12]=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 18923368HCID 18923368, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18923211HCID 18923211, compoundYield 19.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8-[2,6-dichloro-3-(2-pyrrolidon-1-yl)benzyloxy]-2-methylimidazo[1,2-a]pyridine (120 mg) in tetrahydrofuran (3 ml) was added lithium aluminum hydride (19 mg) under ice-cooling, and the mixture was stirred for 2 hours. A saturated aqueous ammonium chloride solution was added thereto, and insoluble material was filtered off. The filtrate was concentrated, and the residue was purified by preparative thin-layer chromatography (5% solution of methanol in methylene chloride) to give 8-[2,6-dichloro-3-(1-pyrrolidinyl)benzyloxy]-2-methylimidazo[1,2-a]pyridine (23 mg).

Workup

  1. temperaturecooling
  2. filtrationinsoluble material was filtered off
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by preparative thin-layer chromatography (5% solution of methanol in methylene chloride)

Sources & evidence

ORD record
ord-34ab7e0f2b1d44a89e1ac39474a07659
Source dataset
uspto-grants-1998_05
Patent number
US05750699

Reaction notes

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