Formic Acid → HCID 13714730, compound

HRID 65095Notes

Reaction equation

HRID 65095 reaction equation
[CH:1]([C:4]([C:24]1[CH:29]=[C:28]([O:30][CH3:31])[C:27]([O:32][CH3:33])=[C:26]([O:34][CH3:35])[CH:25]=1)([CH2:7][CH2:8][CH2:9][NH:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22])[C:5]#[N:6])([CH3:3])[CH3:2].C=O.[CH:38](O)=O.C(=O)([O-])[O-].[K+].[K+]>O>[CH:1]([C:4]([C:24]1[CH:29]=[C:28]([O:30][CH3:31])[C:27]([O:32][CH3:33])=[C:26]([O:34][CH3:35])[CH:25]=1)([CH2:7][CH2:8][CH2:9][N:10]([CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22])[CH3:38])[C:5]#[N:6])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 13714726HCID 13714726, compound

Product 1

HCID 13714730HCID 13714730, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2.58 g of alpha-isopropyl-alpha-[3-[N-[3-(2-nitrophenoxy)propyl]amino]propyl]-3,4,5-trimethoxyphenylacetonitrile, 4.35 ml of 37% of formalin, and 4.35 ml of 90% formic acid was stirred for 1 hour at 90° C. After cooling, to the mixture were added water and potassium carbonate to make it alkaline. The solution was extracted with chloroform and the extract was washed with water, dried, and evaporated. The residue was chromatographed on silica gel using 1% methanol-chloroform as an eluent to give 1.43 g of the desired compound as a yellow oil.

Workup

  1. temperatureAfter cooling, to the mixture
  2. extractionThe solution was extracted with chloroform
  3. washthe extract was washed with water
  4. customdried
  5. customevaporated
  6. customThe residue was chromatographed on silica gel using 1% methanol-chloroform as an eluent

Sources & evidence

ORD record
ord-5983842ea241493c865f5382b3a6641a
Source dataset
uspto-grants-1986_09
Patent number
US04612329

Reaction notes

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