Aniline → 25069-30-1

HRID 412791Notes

Reaction equation

HRID 412791 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[CH3:9][O:8][C:6]([C:5]1[CH:10]=[CH:11][C:2]([N:12]([C:2]2[CH:11]=[CH:10][CH:5]=[CH:4][CH:3]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:3][CH:4]=1)=[O:7]

Participants

6

Reactant 3

HCID 6115AnilineHCID 14307Methyl 4-chlorobenzoateHCID 62657Potassium Phosphate, Tribasic

Product 1

HCID 511056725069-30-1Yield 140.7%

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

According to the general procedure A, methyl 4-chlorobenzoate (88 mg, 0.52 mmol) reacted with aniline (57 mg, 0.61 mmol) using 1 mol % of Pd(dba)2, 2 mol % of Ph5FcP(t-Bu)2, and K3PO4 (260 mg, 1.23 mmol) in DME at 100° C. for 24 h to give the title compound (111 mg, 96%) as a solid: 1H-NMR (400 MHz, CDCl3): δ 7.94 (d, 2H, J=7.6 Hz), 7.35 (t, 2H, J=6.0 and 7.6 Hz), 7.19 (d, 2H, J=7.6 Hz), 7.08 (t, 1H, J=7.6 Hz), 7.01 (d, 2H, J=8.8 Hz), 6.27 (bs, 1H), 3.89 (s, 3H). 13C{1H}-NMR (100 MHz, CDCl3): δ 166.97, 148.06, 140.75, 131.36, 129.37, 122.91, 120.74, 120.27, 114.41, 51.65. GC/MS(EI): m/z 227 (M+).

Workup

  1. customat 100° C.
  2. customfor 24 h

Sources & evidence

ORD record
ord-17c35859f522448ab1c5afba3ad6683b
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

Loading…