3-Nitroaniline → HCID 66816719, compound

HRID 1697101Notes

Reaction equation

HRID 1697101 reaction equation
Cl[C:2]1[C:7]([C:8](=[O:10])[CH3:9])=[CH:6][CH:5]=[C:4]([CH3:11])[N:3]=1.[N+:12]([C:15]1[CH:16]=[C:17]([NH2:21])[CH:18]=[CH:19][CH:20]=1)([O-:14])=[O:13].C([O-])([O-])=O.[Ca+2].CCN(CC)CC>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].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>[CH3:11][C:4]1[N:3]=[C:2]([NH:21][C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([N+:12]([O-:14])=[O:13])[CH:16]=2)[C:7]([C:8](=[O:10])[CH3:9])=[CH:6][CH:5]=1

Participants

8

Reactant 4

HCID 74233-NitroanilineHCID 8471TriethylamineHCID 10112Calcium CarbonateHCID 53402535HCID 53402535, compound

Product 1

HCID 66816719HCID 66816719, compoundYield 31.3%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 634876Binap, (A+-)-CatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

1-(2-Chloro-6-methyl-pyridin-3-yl)-ethanone (0.4 g) was mixed with 3-nitro-phenylamine (0.33 g), Pd(OAc)2 (16 mg), BINAP (45 mg), CaCO3 (0.25 g), and Et3N (0.2 mL) in toluene (10 mL), and heated at 100° C. for 4 d. The product was then filtered and concentrated to provide 1-[6-methyl-2-(3-nitrophenylamino)-pyridin-3-yl]-ethanone (0.2 g).

Workup

  1. filtrationThe product was then filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-bc0f25d948754daca95c1991e4aa0155
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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