Formic Acid → HCID 21430413, compound

HRID 437191Notes

Reaction equation

HRID 437191 reaction equation
Cl.[C:2]([N:5]([CH2:15][CH:16]1[O:21]CCNC1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH2:13][CH3:14])(=[O:4])[CH3:3].C=[O:23].[OH-:24].[Na+].[CH:26]([OH:28])=[O:27]>>[C:16]([OH:21])(=[O:23])[C:26]([OH:28])=[O:27].[C:15]([N:5]([CH:2]1[O:4][CH2:3][CH2:2][N:5]([CH3:6])[CH2:3]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH2:13][CH3:14])(=[O:24])[CH3:16]

Participants

5

Reactant 4

HCID 284Formic AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 21430364HCID 21430364, compound

Product 1

HCID 21430413HCID 21430413, compound

Procedure

A mixture of 2-(N-acetyl-2-ethoxyanilino)methylmorpholine hydrochloride (10 g.), formic acid (25 ml.) and formaldehyde (25 ml.; 40% solution) is heated at 95°-100° C. for 8 hours, poured onto ice (ca. 500 g.), basified (pH 11) with sodium hydroxide solution (40%) and extracted with ether (2× 200 ml.; 1× 100 ml.). The ethereal extracts are combined, dried (Na2SO4), filtered and the filtrate is treated with an excess of ethereal oxalic acid solution to give 2-(N-acetyl-2-ethoxyanilino)-4-methylmorpholine hydrogen oxalate, m.p. 186°-187° C. on recrystallisation from ethanol.

Workup

  1. temperatureis heated at 95°-100° C. for 8 hours
  2. additionpoured onto ice (ca. 500 g.)
  3. extractionextracted with ether (2× 200 ml.; 1× 100 ml.)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. additionthe filtrate is treated with an excess of ethereal oxalic acid solution

Sources & evidence

ORD record
ord-b1c857f0ba054832bdb12af6709b490d
Source dataset
uspto-grants-1977_06
Patent number
US04029786

Reaction notes

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