Hydroxyamine hydrochloride → HCID 136338603, compound

HRID 1180349Notes

Reaction equation

HRID 1180349 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][C:11]=2[CH3:17])[CH:5]=[CH:6][C:7]=1[CH:8]=O.Cl.[NH2:19][OH:20]>O1CCCC1.CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][C:11]=2[CH3:17])[CH:5]=[CH:6][C:7]=1[CH:8]=[N:19][OH:20]

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 58978540HCID 58978540, compound

Product 1

HCID 136338603HCID 136338603, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by reacting 3-chloro-4′-hydroxy-2′-methyl-1,1′-biphenyl-4-carbaldehyde (500 mg, 2.03 mmol) with hydroxylamine hydrochloride (425 mg, 6.10 mmol) in anhydrous tetrahydrofuran (50 mL) and methanol (20 mL) according to Method C to yield 350 mg (57% over two steps) of white solid: mp 169-171° C.; 1H NMR (DMSO-d6): δ 2.19 (3H, s), 6.65-6.70 (2H, m), 7.06 (1H, d, J=8.14 Hz), 7.31 (1H, d, J=8.05 Hz), 7.41 (1H, d, J=1.40 Hz), 7.83 (1H, d, J=8.08 Hz), 8.38 (1H, s), 9.51 (1H, s), 11.69 (1H, s); MS (ESI) m/z 260/262 (M−H)−, 262/264 (M+H)+.

Workup

  1. customto yield 350 mg (57% over two steps) of white solid

Sources & evidence

ORD record
ord-706b3222dcb348cdbaefe853c9c54b58
Source dataset
uspto-grants-2007_10
Patent number
US07279600B2

Reaction notes

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