Trichloroacetic Acid → Methyl 5-[cyanohydroxy(4-methylphenyl)methyl]-1-methylpyrrole-2-acetate

HRID 848040Notes

Reaction equation

HRID 848040 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([C:8]#[N:9])=[O:7])=[CH:4][CH:3]=1.[CH3:12][N:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[CH2:18][C:19]([O:21][CH3:22])=[O:20].ClC(Cl)(Cl)C(O)=O>CCOCC>[C:8]([C:6]([OH:7])([C:5]1[CH:10]=[CH:11][C:2]([CH3:1])=[CH:3][CH:4]=1)[C:17]1[N:13]([CH3:12])[C:14]([CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:15][CH:16]=1)#[N:9]

Participants

5

Reactant 3

HCID 6421Trichloroacetic AcidHCID 103992Methyl 1-methylpyrrol-2-acetateHCID 641326Oxo-P-tolyl-acetonitrile

Product 1

HCID 12940095Methyl 5-[cyanohydroxy(4-methylphenyl)methyl]-1-methylpyrrole-2-acetateYield 16%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 1.45 g (0.01 mole) of 4-methylbenzoylcyanide, 1.5 g (0.01 mole) of methyl 1-methylpyrrole-2-acetate and 40 mg (0.25 mmoles) of trichloroacetic acid in 4 ml of ether was stirred at 25° under nitrogen for 21 days. The precipitated solid was collected by filtration and washed with cold ether, than hexane. The combined filtrates were evaporated in vacuo. A second crop of crystals was taken from hexane. After recrystallization from toluene:hexane was obtained, 0.46 g (16 percent yield) of methyl 5-[cyanohydroxy(4-methylphenyl)-methyl]-1-methylpyrrole-2-acetate mp 117°-118°. H1NMR CDCl3 2.35 (s, 3 H); 3.35 (s, 3 H); 3.55 (s, 2H); 3.65 (s, 3 H); 5.90 (d, 1 H); 6.05 (d, 1H); 7.15 (d, 2H); 7.35 (d, 2H). MS m/e 281, 280, 266, 212 IRnujol 3425, 1700 cm-1.

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. washwashed with cold ether, than hexane
  3. customThe combined filtrates were evaporated in vacuo
  4. customAfter recrystallization from toluene
  5. customhexane was obtained

Sources & evidence

ORD record
ord-b2dca4c3d0d54749a8892380e6b6ad9b
Source dataset
uspto-grants-1981_10
Patent number
US04294760

Reaction notes

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