3,4-Dimethylaniline → HCID 62682340, compound

HRID 1514916Notes

Reaction equation

HRID 1514916 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=O.[CH3:14][C:15]1[CH:16]=[C:17]([CH:19]=[CH:20][C:21]=1[CH3:22])[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.[OH-].[Na+]>CN(C=O)C>[CH3:14][C:15]1[CH:16]=[C:17]([NH:18][C:5](=[O:7])[C:4]2[CH:8]=[CH:9][C:10]([N+:11]([O-:13])=[O:12])=[C:2]([F:1])[CH:3]=2)[CH:19]=[CH:20][C:21]=1[CH3:22]

Participants

7

Reactant 5

HCID 72483,4-DimethylanilineHCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2306533-Fluoro-4-nitrobenzoic acid

Product 1

HCID 62682340HCID 62682340, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-fluoro-4-nitrobenzoic acid (2 g), 3,4-dimethylaniline (1.25 g), BOP (5.45 g) and DIEA (2.69 mL) in DMF (20 mL) was stirred at room temperature for 20 h. Then 1N NaOH aqueous solution was added (pH˜12). The aqueous layer was extracted with EtOAc. The organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was washed with CH2Cl2/MeOH mixture, and the solid was filtered to give N-(3,4-dimethyl-phenyl)-3-fluoro-4-nitrobenzamide as a yellow solid: MS (m/z) 289 (M+1); 1H NMR (DMSO-d6, 400 MHz) δ 10.39 (s, 1H), 8.30 (t, 1H), 8.10 (d, 1H), 7.97 (d, 1H), 7.53 (s, 1H), 7.49 (d, 1H), 7.13 (d, 1H), 2.23 (s, 3H), 2.20 (s, 3H).

Workup

  1. extractionThe aqueous layer was extracted with EtOAc
  2. washThe organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. washThe crude product was washed with CH2Cl2/MeOH mixture
  7. filtrationthe solid was filtered

Sources & evidence

ORD record
ord-e7734fbd3e0f456291feee70119aef19
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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