Ammonium Chloride → HCID 19364897, compound

HRID 1531002Notes

Reaction equation

HRID 1531002 reaction equation
[C:1]([C:9]1[C:10](=[O:25])[C:11]2[CH:12]=[CH:13][CH:14]=[C:15]3[C:23]=2[N:22]([CH:24]=1)[C:21]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]3=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+]>O1CCCC1>[OH:8][CH:1]([C:9]1[C:10](=[O:25])[C:11]2[CH:12]=[CH:13][CH:14]=[C:15]3[C:23]=2[N:22]([CH:24]=1)[C:21]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]3=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 21252825HCID 21252825, compound

Product 1

HCID 19364897HCID 19364897, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-benzoyl-4H-pyrido[3,2,1-jk]carbazole-4-one (80 mg) produced in Example 145 was dissolved in anhydrous tetrahydrofuran (80 ml), and lithium aluminium tri-t-butoxyhydride (76 mg) was added to the solution in an ice bath, and the mixture was stirred for 30 minutes. Saturated aqueous solution of ammonium chloride of an adequate amount was added to the reaction mixture, and the mixture was heated to room temperature, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residual crude crystals were re-precipitated from hexane and ethyl acetate to obtain the title compound (35 mg, 44%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residual crude crystals were re-precipitated from hexane and ethyl acetate

Sources & evidence

ORD record
ord-1603ad8140754eeb8f897cedccb44ee0
Source dataset
uspto-grants-2001_03
Patent number
US06197768B1

Reaction notes

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