2-Nitroaniline → HCID 21956525, compound

HRID 2213087Notes

Reaction equation

HRID 2213087 reaction equation
S(Cl)(Cl)=O.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)[C:10]([OH:12])=O.[N+:22]([C:25]1[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=1[NH2:27])([O-:24])=[O:23].C(N(CC)CC)C>C(Cl)Cl>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)[C:10]([NH:27][C:26]1[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=1[N+:22]([O-:24])=[O:23])=[O:12]

Participants

6

Reactant 4

HCID 69462-NitroanilineHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 219565153-Methoxy-4-(pyridin-2-yl)benzoic acid

Product 1

HCID 21956525HCID 21956525, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To thionyl chloride (20 mL) was added 3-methoxy-4-(pyridin-2-yl)benzoic acid (500 mg, 2.2 mmol). The mixture was heated at reflux for 3 h, cooled to rt, and concentrated. The resultant acid chloride was taken up in 20 mL of CH2Cl2 and the mixture cooled to 0° C. before addition of 2-nitroaniline (301 mg, 2.2 mmol) and triethylamine (0.3 mL, 2.2 mmol), and the solution warmed to rt overnight. The reaction mixture was diluted with CH2Cl2, washed successively with water, saturated Na2CO3, and brine, and the organic layer dried (MgSO4) and concentrated. The crude product was purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (1:1 to 1:1) to afford the desired 3-methoxy-4-(pyridin-2-yl)-2′-nitrobenzanilide as a yellow solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 h
  3. concentrationconcentrated
  4. temperaturethe solution warmed to rt overnight
  5. washwashed successively with water, saturated Na2CO3, and brine
  6. dry with materialthe organic layer dried (MgSO4)
  7. concentrationconcentrated
  8. customThe crude product was purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (1:1 to 1:1)

Sources & evidence

ORD record
ord-d840046b0315462581bdd91286e662d0
Source dataset
uspto-grants-2006_09
Patent number
US07105533B2

Reaction notes

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