Aniline → HCID 69020353, compound

HRID 1865081Notes

Reaction equation

HRID 1865081 reaction equation
ClN1C(=O)CCC1=O.[CH2:9]([O:11][C:12]([C:14]1[N:15]([CH3:32])[C:16]([CH2:30][CH3:31])=[C:17]([C:28]#[N:29])[C:18]=1[C:19]1[CH:24]=[CH:23][C:22]([C:25]([OH:27])=O)=[CH:21][CH:20]=1)=[O:13])[CH3:10].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1>C(Cl)Cl.O>[CH2:9]([O:11][C:12]([C:14]1[N:15]([CH3:32])[C:16]([CH2:30][CH3:31])=[C:17]([C:28]#[N:29])[C:18]=1[C:19]1[CH:20]=[CH:21][C:22]([C:25](=[O:27])[NH:52][C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)=[CH:23][CH:24]=1)=[O:13])[CH3:10]

Participants

7

Reactant 4

HCID 6115AnilineHCID 11776TriphenylphosphineHCID 31398ChlorosuccinimideHCID 69023699HCID 69023699, compound

Product 1

HCID 69020353HCID 69020353, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Add N-chlorosuccinimide (0.13 g, 1.0 mmol) to 3-(4-carboxy-phenyl)-4-cyano-5-ethyl-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (0.33 g, 11.0 mmol, prepared in example E-157) and triphenyl-phosphine (0.26 g, 1.0 mmol) in methylene chloride at 0° C. with stirring. Allow the reaction to warm to room temperature. After 30 minutes, add aniline (0.18 mL, 2.0 mmol). After 2-3 hours, pour the reaction mixture into water and extract with methylene chloride. Combine the organic extracts, wash with water and brine, dry over anhydrous magnesium sulfate, filter, and concentrate under reduced pressure. Purify the residue by flash chromatography eluting with ethyl acetate:hexanes to provide the title compound. Mass spectrum (m/e): 402.0 (M+1).

Workup

  1. customthe reaction
  2. waitAfter 2-3 hours
  3. extractionextract with methylene chloride
  4. washwash with water and brine
  5. dry with materialdry over anhydrous magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under reduced pressure
  8. customPurify the residue by flash chromatography
  9. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-4e44e908ac6a4718ae87adfaba4a0211
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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