Potassium Hydroxide → 3-Acetyl-beta-carboline-oxime

HRID 1903104Notes

Reaction equation

HRID 1903104 reaction equation
[OH-].[K+].[C:3]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH:18]=1)=[CH:15][CH:14]=[CH:13][CH:12]=3)(=O)[CH3:4].[OH:19][NH:20]Cl>CO>[C:3](=[N:20][OH:19])([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH:18]=1)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH3:4]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 149953Hydroxylamine, N-chloro-HCID 127891461-(9H-beta-Carbolin-3-yl)ethan-1-one

Product 1

HCID 1363992773-Acetyl-beta-carboline-oximeYield 65.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 1.0 g of potassium hydroxide in 25 ml of methanol, there is added a mixture of 0.85 g of 3-acetyl-β-carboline, 75 ml of methanol and 1.0 g of hydroxyamino hydrochloride. The reaction mixture is allowed to stand for 4 hours at room temperature. After evaporation, water is added and then the mixture is brought to pH 7 with glacial acetic acid. The solid reaction product is filtered and washed with water and ether. 0.6 g of 3-acetyl-β-carboline-oxime with an m.p. of 250° C. (decomposition) is obtained. In analogous manner there is obtained: 3-pentanoyl-β-carboline-oxime, m.p. 95°-120° C.

Workup

  1. customAfter evaporation, water
  2. additionis added
  3. customThe solid reaction product
  4. filtrationis filtered
  5. washwashed with water and ether

Sources & evidence

ORD record
ord-19026031f8944776a9933a63ded3bb75
Source dataset
uspto-grants-1984_03
Patent number
US04435403

Reaction notes

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