Hydroxylamine → HCID 21399922, compound

HRID 1076185Notes

Reaction equation

HRID 1076185 reaction equation
[NH2:1][OH:2].CC[O-].[Na+].[Cl:7][C:8]1[C:20]([CH3:21])=[C:19]2[C:11]([C:12]3[CH:13]=[CH:14][CH:15]=[C:16]([C:22]([OH:24])=O)[C:17]=3[NH:18]2)=[CH:10][CH:9]=1>C(O)C>[Cl:7][C:8]1[C:20]([CH3:21])=[C:19]2[C:11]([C:12]3[CH:13]=[CH:14][CH:15]=[C:16]([C:22]([NH:1][OH:2])=[O:24])[C:17]=3[NH:18]2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 2723922Sodium ethoxideHCID 213999317-Chloro-8-methylcarbazole-1-carboxylic acid

Product 1

HCID 21399922HCID 21399922, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Under cooling, a solution of 200 mg. of hydroxylamine in 15 ml. of ethanol is combined with 10 ml. of a sodium ethylate solution containing 1% sodium, as well as, in incremental portions, with 1.0 g. of the ethyl ester of 7-chloro-8-methylcarbazole-1-carboxylic acid. The mixture is stirred for one hour at 0° C. and for another 12 hours at room temperature and is then concentrated under vacuum. The residue is taken up in water, acidified to pH 1 with hydrochloric acid, extracted with ethyl acetate, and the extract is washed and concentrated. The residue is recrystallized from ethanol - water, thus obtaining in a 20% yield, 7-chloro-8-methylcarbazole-1-carbohydroxamic acid, m.p. 200° C.

Workup

  1. temperatureUnder cooling
  2. concentrationis then concentrated under vacuum
  3. extractionextracted with ethyl acetate
  4. washthe extract is washed
  5. concentrationconcentrated
  6. customThe residue is recrystallized from ethanol - water

Sources & evidence

ORD record
ord-2fde4616f8b94648b5a523a746bc189d
Source dataset
uspto-grants-1976_05
Patent number
US03956295

Reaction notes

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