Hydroxyamine hydrochloride → HCID 178513279, compound

HRID 423299Notes

Reaction equation

HRID 423299 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][NH:7]2)#[N:2].C(=O)([O-])O.[Na+].Cl.[NH2:18][OH:19]>C(O)C>[OH:19][NH:18][C:1]([C:3]1[C:4]2[CH:5]=[CH:6][NH:7][C:8]=2[CH:9]=[CH:10][CH:11]=1)=[NH:2]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochloride2×HCID 516892Sodium Bicarbonate2×HCID 38176024-Cyanoindole

Product 1

HCID 178513279HCID 178513279, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 4-cyanoindole (5.0 g, 35.2 mmol), sodium hydrogen carbonate (8.9 g, 105.6 mmol) and hydroxylamine hydrochloride (4.9 g, 70.4 mmol) in ethanol (200 ml) was heated at 55° C. overnight. Sodium hydrogen carbonate (5.9 g, 70 mmol) and hydroxylamine hydrochloride (4.9 g, 70.4 mmol) was added. The mixture was heated for 4 days until only a small amount of starting material was present. The inorganics were filtered off, washing the solid well with ethanol and evaporated off the solvent. The residue was triturated with diethyl ether to give 5.8 g of off-white solid. δH (400 MHz, methanol-d4) 6.76-6.78 (1H, m), 7.12 (1H, t), 7.24 (1H, dd), 7.29-7.33 (1H, m) 7.46 (1H, dd).

Workup

  1. temperatureThe mixture was heated for 4 days until only a small amount of starting material
  2. filtrationThe inorganics were filtered off
  3. washwashing the solid well with ethanol
  4. customevaporated off the solvent
  5. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-2688f0e8411744959a4f47a9322be5a0
Source dataset
uspto-grants-2012_01
Patent number
US08101775B2

Reaction notes

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