Formic Acid → HCID 21292418, compound

HRID 622309Notes

Reaction equation

HRID 622309 reaction equation
[CH3:1][N:2]([CH:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[CH2:3][C:4](O)=O.[CH:20]([OH:22])=[O:21].CC1C=CC=CC=1C.[OH2:31]>>[CH3:4][CH:3]([C:20]([OH:22])=[O:21])[N:2]([CH:1]=[O:31])[CH:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1

Participants

5

Reactant 4

HCID 284Formic AcidHCID 962WaterHCID 7237O-XyleneHCID 65056421methyl N-[phenyl(2-pyridinyl)methyl]glycine

Product 1

HCID 21292418HCID 21292418, compoundYield 60.3%

Procedure

A mixture of 37 parts of methyl N-[phenyl(2-pyridinyl)methyl]glycine, 36 parts of formic acid and 450 parts of dimethylbenzene was stirred and refluxed for 2 hours. The reaction mixture was poured into water. The product was extracted with 1,1'-oxybisethane. The extract was washed successively with a sodium hydroxide solution 10% and water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 24 parts (60.3%) of methyl N-formyl-N-[phenyl(2-pyridinyl)methyl]glycine as a residue.

Workup

  1. temperaturerefluxed for 2 hours
  2. extractionThe product was extracted with 1,1'-oxybisethane
  3. washThe extract was washed successively with a sodium hydroxide solution 10% and water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated

Sources & evidence

ORD record
ord-05ff2a6188c043f3adb70271c4557ef7
Source dataset
uspto-grants-1988_09
Patent number
US04770689

Reaction notes

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