Hydroxyamine hydrochloride → HCID 178470832, compound

HRID 1512745Notes

Reaction equation

HRID 1512745 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]([CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[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]([CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:14]2

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochloride2×HCID 516892Sodium Bicarbonate2×HCID 67025284ethyl 3-(5-cyano-1H-indol-2-yl)propanoate

Product 1

HCID 178470832HCID 178470832, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Hydroxylamine hydrochloride (121 mg) and sodium bicarbonate (293 mg) was added to a solution of ethyl 3-(5-cyano-1H-indol-2-yl)propanoate (D30) (200 mg) in EtOH (15 mL), in that sequence. The reaction mixture was heated to 50° C. and stirred for 72 hours at that temperature. Another portion of hydroxylamine hydrochloride (60 mg) was added, followed by addition of sodium bicarbonate (150 mg). The resulting suspension was stirred at 50° C. for 24 hours. The inorganics was filtered off. The solid was washed with dichloromethane. The filtrate was concentrated to afford a pale yellow oil. Trituration of the residue provided ethyl 3-{5-[(hydroxyamino)(imino)methyl]-1H-indol-2-yl}propanoate (D31) (220 mg) as a pale yellow solid.

Workup

  1. stirringThe resulting suspension was stirred at 50° C. for 24 hours
  2. filtrationThe inorganics was filtered off
  3. washThe solid was washed with dichloromethane
  4. concentrationThe filtrate was concentrated
  5. customto afford a pale yellow oil

Sources & evidence

ORD record
ord-eada1423e27a4f69bc4f3118cce4385f
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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