Acetic Acid → HCID 21459172, compound

HRID 725350Notes

Reaction equation

HRID 725350 reaction equation
N1CCCC1.C(O)(=O)C.[OH:10][C:11]1[CH:12]=[C:13]([CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[C:18]=1[OH:19])[CH:14]=O.[O:23]=[C:24]([CH3:42])[CH2:25][CH2:26][CH2:27][CH2:28][C:29]([NH:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=1)=[O:30]>O1CCCC1>[OH:10][C:11]1[CH:12]=[C:13](/[CH:14]=[CH:42]/[C:24](=[O:23])[CH2:25][CH2:26][CH2:27][CH2:28][C:29]([NH:31][C:32]2[CH:33]=[CH:34][C:35]([C:38]([F:39])([F:40])[F:41])=[CH:36][CH:37]=2)=[O:30])[CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[C:18]=1[OH:19]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 57489573,4-Dihydroxy-5-nitrobenzaldehydeHCID 12857136HCID 12857136, compound

Product 1

HCID 21459172HCID 21459172, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.875 ml of pyrrolidine in 35 ml of tetrahydrofuran is treated at 5° with 0.605 ml of acetic acid and subsequently with 1.73 g of 3,4-dihydroxy-5-nitrobenzaldehyde and 2.87 g of 6-oxo-4'-(trifluoromethyl)heptananilide and stirred at 23° under argon for 56 hours. The residue obtained after evaporating the reaction mixture is partitioned between ethyl acetate and 1N sodium hydroxide solution. The combined sodium hydroxide extracts are made acid with conc. hydrochloric acid, extracted with ethyl acetate, the combined ethyl acetate extracts are washed with saturated sodium chloride solution, dried over sodium sulfate, evaporated and the residue is chromatographed on 120 g of silica gel with methylene chloride/methanol (91:9). After recrystallization atom ethyl acetate/petroleum ether there is obtained (E)-8-(3,4-dihydroxy-5-nitrophenyl)-6-oxo-4'-(trifluoromethyl)-7-octenanilide of m.p. 194°-197°.

Workup

  1. customThe residue obtained
  2. customafter evaporating the reaction mixture
  3. customis partitioned between ethyl acetate and 1N sodium hydroxide solution
  4. extractionextracted with ethyl acetate
  5. washthe combined ethyl acetate extracts are washed with saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customthe residue is chromatographed on 120 g of silica gel with methylene chloride/methanol (91:9)
  9. customAfter recrystallization atom ethyl acetate/petroleum ether there

Sources & evidence

ORD record
ord-8c69ca8c1d4b409f9e1341004b930454
Source dataset
uspto-grants-1998_01
Patent number
US05705703

Reaction notes

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