Potassium Hydroxide → 6-Benzyloxy-4-methoxymethyl-beta-carboline-3-carbaldehyde Oxime

HRID 2107050Notes

Reaction equation

HRID 2107050 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]1[CH:16]=[N:15][C:14]([CH:22]=O)=[C:13]([CH2:24][O:25][CH3:26])[C:12]2=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:28][OH:29].[OH-].[K+]>CN(C)C=O.C(O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]1[CH:16]=[N:15][C:14]([CH:22]=[N:28][OH:29])=[C:13]([CH2:24][O:25][CH3:26])[C:12]2=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 143729316-Benzyloxy-4-methoxymethyl-beta-carboline-3-carbaldehyde

Product 1

HCID 1363646136-Benzyloxy-4-methoxymethyl-beta-carboline-3-carbaldehyde Oxime

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

13.5 g of 6-benzyloxy-4-methoxymethyl-β-carboline-3-carbaldehyde is dissolved in 150 ml of dry dimethyl formamide (DMF) and there are added thereto 6 g of hydroxylamine hydrochloride and a solution of 6 g of potassium hydroxide in 30 ml of ethanol. The reaction mixture is stirred for one hour at room temperature, filtered, and the residue washed with 2×20 ml of DMF. The DMF fraction is combined with 200 ml of ice water, the precipitate is filtered off, washed with water, and dried. Yield: 9.6 g.

Workup

  1. additionthere are added
  2. filtrationfiltered
  3. washthe residue washed with 2×20 ml of DMF
  4. filtrationthe precipitate is filtered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-1be2b4d12a3b4bb495b504f337e2fb7f
Source dataset
uspto-grants-1990_06
Patent number
US04933345

Reaction notes

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