Acetanilide → HCID 762824, compound

HRID 1931264Notes

Reaction equation

HRID 1931264 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7](Cl)=[C:6]([N+:11]([O-])=O)[CH:5]=1.[C:15]1([NH:21][C:22](=O)[CH3:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[Cs+].[Cs+]>FC(F)(F)C([O-])=O.[Pd+2].FC(F)(F)C([O-])=O.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[N:21]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:22]([CH3:23])=[N:11][C:6]=2[CH:5]=1)=[O:14]

Participants

6

Reactant 3

HCID 904AcetanilideHCID 10796Cesium carbonateHCID 735797Methyl 4-chloro-3-nitrobenzoate

Product 1

HCID 762824HCID 762824, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 634876Binap, (A+-)-CatalystHCID 2733347Palladium(II) trifluoroacetateCatalyst

Procedure

The title compound was prepared following Method A at larger scale, from 4-chloro-3-nitrobenzoic acid methyl ester (5.39 g, 25 mmol), N-phenylacetamide (3.38 g, 25 mmol), palladium trifluoroacetate (416 mg, 1.25 mmol), BINAP (778 mg, 1.25 mmol) and Cs2CO3 11.4 g, 35 mmol) and refluxing just for 5 hours, giving rise to the title compound as colorless crystals (5.19 g, 78%). mp 108° C. to 110° C. 1H NMR (DMSO) δ 2.55 (s, 3H), 3.78 (s, 3H), 7.30 (d, J=8.2Hz, 1H), 7.52-7.71 (m, 5H), 7.92 (d, J=8.2Hz, 1H), 8.30 (br s, 1H); 13C NMR δ 13.6, 52.1, 110.8, 118.5, 124.7, 124.8, 127.0, 129.7, 130.1, 134.0, 137.9, 153.7, 157.8, 166.2. HRMS (FAB): cal. for C16H15N2O2 [M+H+]: 267.1134; found: 267.1128.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-fe779afdd25a4aa790bed4b189406b7b
Source dataset
uspto-grants-2012_05
Patent number
US08188282B2

Reaction notes

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