Ammonium Chloride → HCID 19696324, compound

HRID 863688Notes

Reaction equation

HRID 863688 reaction equation
[BH4-].[Na+].[CH:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[C:6]1[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][N:7]12.[Cl-].[NH4+]>CO>[OH:16][CH:13]1[CH2:12][N:7]2[C:8]3[C:4]([CH:5]=[C:6]2[CH2:15][CH2:14]1)=[CH:3][CH:11]=[CH:10][CH:9]=3

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 15063399HCID 15063399, compound

Product 1

HCID 19696324HCID 19696324, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

190 mg of sodium borohydride were added to a stirred solution of 650 mg of 8,9-dihydropyrido[1,2-a]indol-7(6H)-one in 50 ml of methanol under a nitrogen atmosphere. The mixture was stirred and then poured into 100 ml of saturated ammonium chloride solution. The mixture was extracted with ethyl acetate and the combined extracts were dried and evaporated to give a solid. This was crystallized from diethyl ether/n-hexane and gave 500 mg of 6,7,8,9-tetrahydro-7-hydroxypyrido[1,2-a]indole of melting point 99°-100° C.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. customthe combined extracts were dried
  3. customevaporated
  4. customto give a solid
  5. customThis was crystallized from diethyl ether/n-hexane

Sources & evidence

ORD record
ord-b5adaf414ebb434f9d58328bd331df10
Source dataset
uspto-grants-1998_02
Patent number
US05721245

Reaction notes

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