Water → HCID 21953530, compound

HRID 1280195Notes

Reaction equation

HRID 1280195 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[NH2:10][OH:11].Cl.[OH-].[K+].O>CO.C1COCC1>[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][NH:10][OH:11]

Participants

7

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 2526103-IodobenzaldehydeHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 21953530HCID 21953530, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

3-Iodobenzaldehyde prepared above (8.1 g, 34.9 mmol) was dissolved in 50 mL MeOH and 20 mL THF. After addition of H2NOH.HCl (10 mL H2O) and 6N KOH, an additional 20 mL H2O, 10 mL THF, and 10 mL MeOH were added. The product was recovered as a white solid (7.96 g, 91.6%, 92% desired product). mp: 63.0-70.0° C. IR (film): 3256, 3056, 2857, 1591, 1564, 1470, 1420, 1063, 995, 777. 1H-NMR (400 MHz, CDCl3): δ 7.73 (t, 1H, J=1.6, C6-H), 7.63 (dt, 1H, J=7.9, 1.3, C5-H), 7.31 (d, 1H, J=7.6, C7-H), 7.09 (t, 1H, J=7.8, C6-H), 5.5 (br s, 1H, C1-NHOH), 5.1 (br s, 1H, C1-NHOH), 3.98 (s, 2H, C1-H2). 13C-NMR (100 MHz, CDCl3): δ 139.9,137.9, 136.6, 130.2, 128.2, 94.4, 57.4. EI-MS m/z (rel int): 249 (M+, 65), 217 ([M−NHOH]+, 100). CI-MS (NH3) m/z (rel int): 284 ([M+2NH3+H]+, 28), 267 ([M+NH4]+, 100), 250 ([M+H]+, 45).

Workup

  1. customThe product was recovered as a white solid (7.96 g, 91.6%, 92% desired product)

Sources & evidence

ORD record
ord-723a3802a2f04babbab0aa9d62c8b2e3
Source dataset
uspto-grants-2002_09
Patent number
US06448443B1

Reaction notes

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