Hydroxyamine hydrochloride → HCID 59034617, compound

HRID 75798Notes

Reaction equation

HRID 75798 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH:5]=O.Cl.[NH2:14][OH:15]>CO>[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])/[CH:5]=[N:14]/[OH:15]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 111945283-Methyl-4-nitrobenzaldehyde

Product 1

HCID 59034617HCID 59034617, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a warm solution of 3-methyl-4-nitrobenzaldehyde (1.0 equiv.) in methanol was added hydroxylamine hydrochloride (2.0 equiv.) and the mixture was stirred at 65° C. for 2 hours. Methanol was evaporated and the residue was diluted with ethyl acetate. The organic layer was washed with water, brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was then recrystallized from ethyl acetate and petroleum ether 60-80, to provide the title compound as a creamish solid (81%); 1H NMR (300 MHz, CDCl3) δ: 2.62 (s, 3H), 7.54-7.56 (m, 2H), 7.89 (s, 1H), 7.98-8.01 (d, J=9.0 Hz, 1H), 8.14 (s, 1H); IR (KBr) 3375, 3207, 3087, 2994, 1607, 1585, 1506, 1384, 1319, 1161, 986, 841, 755 cm−1.

Workup

  1. customMethanol was evaporated
  2. additionthe residue was diluted with ethyl acetate
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was then recrystallized from ethyl acetate and petroleum ether 60-80

Sources & evidence

ORD record
ord-110b88133b064c6e92bebe98f59d1ccc
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Reaction notes

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