Methanol → HCID 21458970, compound

HRID 1781813Notes

Reaction equation

HRID 1781813 reaction equation
[OH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11](=[O:15])[C:12]([OH:14])=[O:13])=[CH:4][C:3]=1[O:16][CH3:17].[CH3:18]O>CN(C)C=O.CN(C)C1C=CN=CC=1>[OH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11](=[O:15])[C:12]([O:14][CH3:18])=[O:13])=[CH:4][C:3]=1[O:16][CH3:17]

Participants

5

Reactant 2

HCID 887MethanolHCID 21459072HCID 21459072, compound

Product 1

HCID 21458970HCID 21458970, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

2.42 g of 4-hydroxy-3-methoxy-5-nitrophenylglyoxylic acid are dissolved in 25 ml of dry N,N-dimethylformamide, treated at room temperature with 50 mg of 4-dimethylaminopyridine and 920 mg of dry methanol, subsequently cooled to 0° with an ice-bath and 2.27 g of N,N-dicyclohexylcarbodiimide are added thereto. After 10 minutes the ice-bath is removed and the reaction mixture is stirred for a further 1 hour at room temperature. The mixture is subsequently evaporated. The residue is dissolved in ethyl acetate, whereupon insoluble urea is filtered, the filtrate is washed four times with water, dried over sodium sulfate, filtered and evaporated. There is obtained methyl 4-hydroxy-3-methoxy-5-nitrophenylglyoxylate of m.p. 155°-157° (from methylene chloride/ether).

Workup

  1. temperaturesubsequently cooled to 0° with an ice-bath
  2. customAfter 10 minutes the ice-bath is removed
  3. customThe mixture is subsequently evaporated
  4. dissolutionThe residue is dissolved in ethyl acetate, whereupon insoluble urea
  5. filtrationis filtered
  6. washthe filtrate is washed four times with water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-06921af03d4d48e7a343702b914bbf0e
Source dataset
uspto-grants-1997_05
Patent number
US05633371

Reaction notes

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