Hydroxylamine → Methyl 4-[(hydroxyimino)methyl]-1-naphthalenecarboxylate

HRID 1958867Notes

Reaction equation

HRID 1958867 reaction equation
[NH2:1][OH:2].[CH:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:15]([O:17][CH3:18])=[O:16])=[CH:7][CH:6]=1)=O>CO>[OH:2][N:1]=[CH:3][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:15]([O:17][CH3:18])=[O:16])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 103308541-Naphthalenecarboxylic acid, 4-formyl-, methyl ester

Product 1

HCID 86645276Methyl 4-[(hydroxyimino)methyl]-1-naphthalenecarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of hydroxylamine (1.33 mL, 50% in water) was added to a stirred solution of methyl 4-formyl-1-naphthalenecarboxylate (2.2 g, prepared as described in Journal of Medicinal Chemistry 2002, 45(26), 5755-5775) in methanol (50 mL). After stirring at room temperature for 2 h, the reaction mixture was concentrated under reduced pressure to provide the title compound as a pale yellow solid (2.55 g). 1H NMR (CDCl3): δ 8.93 (d, 1H), 8.86 (s, 1H), 8.41 (d, 1H), 8.14 (d, 1H), 7.82 (d, 1H), 7.63 (m, 2H), 4.02 (s, 3H).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c984d80e4f6f4e2b9906c1836a243ea3
Source dataset
uspto-grants-2013_04
Patent number
US08410153B2

Reaction notes

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