Hydroxyamine hydrochloride → HCID 178468512, compound

HRID 1512737Notes

Reaction equation

HRID 1512737 reaction equation
Cl.[NH2:2][OH:3].C(=O)(O)[O-].[Na+].[C:9]([C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:14]2)#[N:10]>CCO>[OH:3][NH:2][C:9](=[NH:10])[C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:14]2

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochloride2×HCID 516892Sodium Bicarbonate2×HCID 4714953Ethyl 5-cyanoindole-2-carboxylate

Product 1

HCID 178468512HCID 178468512, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

Hydroxylamine hydrochloride (172 mg) and sodium bicarbonate (415 mg) was added to a solution of ethyl 5-cyano-1H-indole-2-carboxylate (D21) (265 mg) in EtOH (15 mL), in that sequence. The reaction mixture was heated to 55° C. and stirred for 16 hours at that temperature. Another portion of hydroxylamine hydrochloride (69.4 mg) was added, followed by addition of sodium bicarbonate (125.5 mg). The resulting suspension was stirred at 55° C. for 12 hours. The inorganics was filtered off. The solid was washed with dichloromethane (30 mL) and methanol (30 mL). The filtrate was concentrated to afford ethyl 5-[(hydroxyamino)(imino)methyl]-1H-indole-2-carboxylate (D22) (280 mg) as a yellow solid. No purification was attempted. MS (ES): C12H13N3O3 requires 247; found 248.1 (M+H+).

Workup

  1. stirringThe resulting suspension was stirred at 55° C. for 12 hours
  2. filtrationThe inorganics was filtered off
  3. washThe solid was washed with dichloromethane (30 mL) and methanol (30 mL)
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-ec9cf9307a3c4b618379dee656de2344
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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