Hydroxylamine → HCID 76804434, compound

HRID 1505264Notes

Reaction equation

HRID 1505264 reaction equation
[C:1]([O:5][C:6]([C:8]1[C:17]2[C:12](=[C:13]([CH:18]=O)[CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:20][OH:21]>C(O)C>[C:1]([O:5][C:6]([C:8]1[C:17]2[C:12](=[C:13]([CH:18]=[N:20][OH:21])[CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 58497917HCID 58497917, compound

Product 1

HCID 76804434HCID 76804434, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-formyl-1-naphtoic acid tert-butyl ester (Example 9.3) (1.5 g) in ethanol (7.6 ml) was added aqueous hydroxylamine (50% w/v) (0.48 ml) and the reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture was concentrated and the residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate) to give 5-(hydroxyimino-methyl)-1-naphtoic acid tert-butyl ester (1.4 g). 1H-NMR (CDCl3, 400 MHz): 8.90 (d, 1H), 8.81 (s, 1H), 8.62 (d, 1H), 8.10 (d, 1H), 7.80 (d, 1H), 7.50-7.65 (m, 2H), 1.70 (s, 9H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-ab4bfe8951054abc9c2d8b56b2107bad
Source dataset
uspto-grants-2015_12
Patent number
US09216973B2

Reaction notes

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