Trifluoroacetic acid → HCID 178490807, compound

HRID 562587Notes

Reaction equation

HRID 562587 reaction equation
CO[CH:3](OC)[CH2:4][NH:5][C:6](=[O:19])[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)=[O:8].C(O)(C(F)(F)F)=O>CC(O)=O>[OH:19][C:6]1[C:7](=[O:8])[N:9]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)[CH:3]=[CH:4][N:5]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 44902124HCID 44902124, compound

Product 1

HCID 178490807HCID 178490807, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of N1-(2,2-dimethoxyethyl)-N2-(4-methoxybenzyl)oxalamide (7.5 g, 25.3 mmol) and TFA (2.340 mL, 30.4 mmol) in AcOH (160 mL) was stirred at 135° C. in a seal tube for 1.5 hours. After cooling to RT and removal of the volatiles under vacuum, ethyl ether (150 ml) and sat. aq. NaHCO3 solution (150 ml) were added. The resulting precipitate was collected by filtration, washed with H2O (50 ml) and ether (50 ml) prior to drying under high vacuum to yield 3-hydroxy-1-(4-methoxybenzyl)pyrazin-2(1H)-one (5.30 g, 21.68 mmol, 86% yield) as brown solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.17 (1H, br. s.), 7.18 (2H, d), 6.81 (2H, d), 6.46 (1H, d, J=5.77 Hz), 6.23 (1H, br. s.), 4.74 (2H, s), 3.24 (1H, s).

Workup

  1. customremoval of the volatiles under vacuum, ethyl ether (150 ml) and sat. aq. NaHCO3 solution (150 ml)
  2. additionwere added
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with H2O (50 ml) and ether (50 ml)
  5. customto drying under high vacuum

Sources & evidence

ORD record
ord-797ed020a42f4e18b3bebc3225b3cd72
Source dataset
uspto-grants-2011_11
Patent number
US08067420B2

Reaction notes

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