Water → HCID 21953491, compound

HRID 1280194Notes

Reaction equation

HRID 1280194 reaction equation
[I:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[NH2:10][OH:11].Cl.[OH-].[K+].O>CO.C1COCC1>[I:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][NH:10][OH:11]

Participants

7

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 6434392-Iodobenzaldehyde

Product 1

HCID 21953491HCID 21953491, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

2-Iodobenzaldehyde prepared above (10.3 g, 44.4 mmol) was dissolved in 50 mL MeOH and 10 mL THF. After addition of H2NOH.HCl (10 mL H2O) and 6N KOH, an additional 50 mL THF, 30 mL H2O, and 30 mL MeOH were added. The product was recovered as a cloudy orange oil (9.46 g, 85.6%, 90% desired product). IR (film): 3256, 3057, 2872, 1564, 1466, 1435, 1013, 748. 1H-NMR (400 MHz, CDCl3): δ 7.92 (dd, 1H, J=7.8, 1.2, C4-H), 7.58 (dd, 1H, J=7.4, 1.8, C7-H), 7.34 (td, 1H, J=7.4, 1.2, C6-H), 7.00 (td, 1H, J=7.6, 1.8, C5-H), 5.5 (br s, 1H, C1-NHOH), 5.0 (br s, 1H, C1-NHOH), 4.13 (s, 2H, C1-H2). 13C-NMR (100 MHz, CDCl3): δ 139.5, 139.1, 131.0, 129.4, 128.3, 100.1, 62.0. EI-MS m/z (rel int): 249 (M+, 36), 217 ([M−NHOH]+, 100), 122 ([M−I], 30). CI-MS (NH3) m/z (rel int): 284 ([M+2NH3+H]+, 30), 267 ([M+NH4]+, 100), 250 ([M+H]+, 27).

Workup

  1. customThe product was recovered as a cloudy orange oil (9.46 g, 85.6%, 90% desired product)

Sources & evidence

ORD record
ord-102b91f1ee5c440fb7d6fa5ed5c7be53
Source dataset
uspto-grants-2002_09
Patent number
US06448443B1

Reaction notes

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