3-Chloroaniline → HCID 8760959, compound

HRID 1514862Notes

Reaction equation

HRID 1514862 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[Cl:14][C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][CH:21]=1)[NH2:18].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:18][C:17]2[CH:19]=[CH:20][CH:21]=[C:15]([Cl:14])[CH:16]=2)=[O:8])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

7

Reactant 5

HCID 79323-ChloroanilineHCID 74115Benzoic acid, 4-amino-3-nitro-HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 516892Sodium Bicarbonate

Product 1

HCID 8760959HCID 8760959, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-amino-3-nitrobenzoic acid (0.5 g), 3-chloroaniline (0.29 mL), BOP (1.46 g) and DIEA (0.72 mL) in DMF (5 mL) was stirred at room temperature for 20 h. Then saturated NaHCO3 aqueous solution was added. The aqueous layer was extracted with CH2Cl2, and the organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography (SiO2, EtOAc:Hexane=12:88 to 100:0) to give 4-amino-N-(3-chloro-phenyl)-3-nitrobenzamide as a yellow solid: MS (m/z) 292 (M+1); 1H NMR (DMSO-d6, 400 MHz) δ 10.32 (s, 1H), 8.73 (s, 1H), 7.97 (d, 1H), 7.94 (s, 1H), 7.87 (s, 2H), 7.69 (d, 1H), 7.37 (t, 1H), 7.16 (d, 1H), 7.10 (d, 1H).

Workup

  1. extractionThe aqueous layer was extracted with CH2Cl2
  2. dry with materialthe organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography (SiO2, EtOAc:Hexane=12:88 to 100:0)

Sources & evidence

ORD record
ord-059487967b394617adfda270cad1b80f
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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