Potassium Carbonate → 4-Methoxymethyl-5-phenoxy-beta-carboline-3-carboxamidoxime

HRID 2166362Notes

Reaction equation

HRID 2166362 reaction equation
[C:1]([C:3]1[N:4]=[CH:5][C:6]2[NH:7][C:8]3[C:13]([C:14]=2[C:15]=1[CH2:16][O:17][CH3:18])=[C:12]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:11]=[CH:10][CH:9]=3)#[N:2].Cl.[NH2:27][OH:28].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:18][O:17][CH2:16][C:15]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3[O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[NH:7][C:6]=2[CH:5]=[N:4][C:3]=1[C:1](=[N:27][OH:28])[NH2:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 230394773-Cyano-4-methoxymethyl-5-phenoxy-beta-carboline

Product 1

HCID 1362106304-Methoxymethyl-5-phenoxy-beta-carboline-3-carboxamidoxime

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 329 mg (0.001 mol) of 3-cyano-4-methoxymethyl-5-phenoxy-beta-carboline, 100 mg of hydroxylamine hydrochloride, 20 ml of ethanol (99%) and 0.52 ml of a 20% aqueous potassium carbonate solution is refluxed for 22 hours. The reaction mixture is filtered and the filtrate concentrated. The residue is mixed with 10 ml of water, the crystalline solid is filtered off and washed with water.

Workup

  1. temperatureis refluxed for 22 hours
  2. filtrationThe reaction mixture is filtered
  3. concentrationthe filtrate concentrated
  4. additionThe residue is mixed with 10 ml of water
  5. filtrationthe crystalline solid is filtered off
  6. washwashed with water

Sources & evidence

ORD record
ord-6e26e0cbcdb34cd8a2d3ac2635446be7
Source dataset
uspto-grants-1990_07
Patent number
US04945090

Reaction notes

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