Methanol → HCID 22921456, compound

HRID 2258412Notes

Reaction equation

HRID 2258412 reaction equation
CO.[CH:3]([N:6]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([O:17]C)=[O:16])=[CH:11][CH:10]=1)[OH:7])([CH3:5])[CH3:4].[OH-].[Na+]>O>[CH:3]([N:6]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([OH:17])=[O:16])=[CH:11][CH:10]=1)[OH:7])([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 22921455HCID 22921455, compound

Product 1

HCID 22921456HCID 22921456, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A MeOH solution (75 mL) of N-isopropyl-N-(4-carbomethoxybenzyl)-hydroxylamine (13.2 g, 59.1 mmol) was heated to 60° C. and treated with NaOH (2.46 g, 61.5 mol) in water 50 (mL). The reaction was allowed to stir for 18 h under argon and was then filtered, concentrated to remove most of the MeOH, diluted with water (100 mL), an acidified to pH-4.5 with conc H2SO4. The white solid was stirred at ambient temperature for 3 h, isolated by filtration, washed with copious amounts of water and then dried in vacuo at 60° C. to give 10.34 g (83%) N-isopropyl-N-(4-carboxybenzyl)hydroxylamine. mp 201°-202° C.(dec). 1H NMR (DMSO-d6) δ 12.6 (br, 1), 7.83 (d, J=8.1 Hz, 2), 7.49 (s, 1), 7.41 (d, J=8.1 Hz, 2), 3.72 (s, 2), 2.85 (sept, J=6.4 Hz, 1), 1.02 (d, J=6.4 Hz, 6).

Workup

  1. filtrationwas then filtered
  2. concentrationconcentrated
  3. customto remove most of the MeOH
  4. additiondiluted with water (100 mL)
  5. stirringThe white solid was stirred at ambient temperature for 3 h
  6. customisolated by filtration
  7. washwashed with copious amounts of water
  8. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-1ea1c91225be43d2b2b712aead425a76
Source dataset
uspto-grants-1997_08
Patent number
US05660974

Reaction notes

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