Ammonium Chloride → HCID 18321953, compound

HRID 1871129Notes

Reaction equation

HRID 1871129 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][O:9][C:10]2[CH:11]=[CH:12][CH:13]=[C:14]3[C:19]=2[N:18]=[C:17]([CH3:20])[CH:16]=[C:15]3[N:21]2[CH:25]=[CH:24][CH:23]=[N:22]2)=[C:6]([Cl:26])[CH:5]=[CH:4][C:3]=1[N:27]1[CH:31]=[CH:30][CH:29]=[C:28]1[CH:32]=[O:33].[BH4-].[Na+].[Cl-].[NH4+]>CO>[Cl:1][C:2]1[C:7]([CH2:8][O:9][C:10]2[CH:11]=[CH:12][CH:13]=[C:14]3[C:19]=2[N:18]=[C:17]([CH3:20])[CH:16]=[C:15]3[N:21]2[CH:25]=[CH:24][CH:23]=[N:22]2)=[C:6]([Cl:26])[CH:5]=[CH:4][C:3]=1[N:27]1[CH:31]=[CH:30][CH:29]=[C:28]1[CH2:32][OH:33]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 18321810HCID 18321810, compound

Product 1

HCID 18321953HCID 18321953, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-[2,4-dichloro-3-[2-methyl-4-(pyrazol-1-yl)quinolin-8-yloxymethyl]phenyl]-2-formylpyrrole (23 mg) in methanol (0.5 ml) was added sodium borohydride (1.91 mg) udner ice-cooling, and the mixture was stirred for 2 hours. To the mixture was dropwise added aqueous solution of ammonium chloride under ice-cooling, and the mixture was stirred for 1 hour. The mixture was concentrated in vacuo, and ethyl acetate and water were added thereto. The separated organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin layer chromatography (chloroform:methanol=20:1, V/V) to give 1-[2,4-dichloro-3-[2-methyl-4-(pyrazol-1-yl)quinolin-8-yloxymethyl]phenyl]-2-hydroxymethylpyrrole (11 mg) as amorphous powder.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred for 1 hour
  4. concentrationThe mixture was concentrated in vacuo, and ethyl acetate and water
  5. additionwere added
  6. washThe separated organic layer was washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. customThe residue was purified by preparative thin layer chromatography (chloroform:methanol=20:1, V/V)

Sources & evidence

ORD record
ord-4c465ade676e4950b27081fa3c0220d1
Source dataset
uspto-grants-2000_08
Patent number
US06100284

Reaction notes

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