Hydroxyamine hydrochloride → HCID 178513239, compound

HRID 1512740Notes

Reaction equation

HRID 1512740 reaction equation
Cl.[NH2:2][OH:3].C(=O)(O)[O-].[Na+].[OH:9][CH2:10][C:11]1[NH:12][C:13]2[C:18]([CH:19]=1)=[CH:17][C:16]([C:20]#[N:21])=[CH:15][CH:14]=2>CCO>[OH:3][NH:2][C:20]([C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([CH2:10][OH:9])=[CH:19]2)=[NH:21]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochloride2×HCID 516892Sodium Bicarbonate2×HCID 135679562-(hydroxymethyl)-1H-indole-5-carbonitrile

Product 1

HCID 178513239HCID 178513239, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Hydroxylamine hydrochloride (243 mg) and sodium bicarbonate (586 mg) was added to a solution of 2-(hydroxymethyl)-1H-indole-5-carbonitrile (D24) (300 mg) in EtOH (20 mL), in that sequence. The reaction mixture was heated to 50° C. and stirred for 24 hours at that temperature. Another portion of hydroxylamine hydrochloride (100 mg) was added, followed by addition of sodium bicarbonate (220 mg). The resulting suspension was stirred at 50° C. for 7 hours. The inorganics was filtered off. The filtrate was concentrated to afford a pale yellow oil. Trituration of the residue provided N-hydroxy-2-(hydroxymethyl)-1H-indole-5-carboximidamide (D25) (300 mg) as a pale yellow solid. MS (ES): C10H11N3O2 requires 205; found 206.2 (M+H+).

Workup

  1. stirringThe resulting suspension was stirred at 50° C. for 7 hours
  2. filtrationThe inorganics was filtered off
  3. concentrationThe filtrate was concentrated
  4. customto afford a pale yellow oil

Sources & evidence

ORD record
ord-5a5292c9195e4e6886e8769c03960f97
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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