Hydroxylamine → HCID 178511421, compound

HRID 2102470Notes

Reaction equation

HRID 2102470 reaction equation
[C:1]([O:9][CH2:10][C:11]#[N:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:13][OH:14]>C(O)C>[C:1]([O:9][CH2:10][C:11]([NH:13][OH:14])=[NH:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 277773cyanomethyl benzoate

Product 1

HCID 178511421HCID 178511421, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Cyanomethyl benzoate (22.2 g, 138 mmol) was dissolved in ethanol (250 mL) followed by addition of 50% aqueous hydroxylamine (16.9 mL, 276 mmol) and the mixture was stirred for 15 minutes at room temperature. Concentration followed by addition of water (250 mL) afforded a colorless crystalline solid that was collected by filtration and washed with additional water then dried in vacuo to give 2-(hydroxyamino)-2-iminoethyl benzoate (23.69 g, 88% yield). 1H-NMR (400 MHz; DMSO-d6): 9.37 (s, 1H), 7.98 (m, 2H), 7.65 (m, 1H), 7.54 (tr, 2H), 5.69 (br s, 2H), 4.64 (s, 2H).

Workup

  1. concentrationConcentration
  2. additionfollowed by addition of water (250 mL)
  3. customafforded a colorless crystalline solid
  4. filtrationthat was collected by filtration
  5. washwashed with additional water
  6. customthen dried in vacuo

Sources & evidence

ORD record
ord-abb7a71fea93403ba416f446ef755f74
Source dataset
uspto-grants-2009_08
Patent number
US07576074B2

Reaction notes

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