Aniline → HCID 18929218, compound

HRID 1599848Notes

Reaction equation

HRID 1599848 reaction equation
[F:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([NH:12][C:13](=[O:16])[CH2:14]Br)[CH:3]=1.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[OH-].[K+]>CN(C=O)C>[F:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([NH:12][C:13](=[O:16])[CH2:14][NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 14797Potassium HydroxideHCID 18929208HCID 18929208, compound

Product 1

HCID 18929218HCID 18929218, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4,5-difluoro-2-((bromoacetyl)amino)benzoic acid (31.0 g 105.4 mmol) and aniline (24 mL, 24.5 g, 263.4 mmol) in anhydrous DMF (100 mL) was heated to 95°-100° C. overnight with stirring under N2. The solution was cooled, poured into 500 mL of ice-water, and then a solution of 5% KOH was added until the pH of the solution was 10. The solution was extracted with 3×150 mL of CH2Cl2, and then the aqueous layer was separated and acidified to pH=3 using 2N HCl. The yellow precipitate which formed was filtered, washed with water, and then dried in a vacuum desiccator to yield 32.01 g (99%) of the title compound as a light-yellow solid, mp 124°-126° C.: 1H NMR (DMSO-d6) δ12.10 (s, 1H), 8.75 (dd, J=14.0, J=7.6, 1H), 7.86 (dd, J=11.6, J=1.2, 1H), 7.09 (t, J=7.2, 2H), 6.63-6.40 (m, 4H), 3.85 (s, 2H); 13C NMR (DMSO-d6) δ171.40, 167.44, 152.18 (dd, J=249, J=12.7), 148.02, 144.02 (dd, J=242, J=12.6), 138.18 (dd, J=10.6, J=2.1), 129.01, 119.66 (d, J=19), 117.22, 113.10, 112.48, 108.21 (d, J=23), 48.82; MS (El, m/z) 306 (M+).

Workup

  1. temperatureThe solution was cooled
  2. extractionThe solution was extracted with 3×150 mL of CH2Cl2
  3. customthe aqueous layer was separated
  4. customThe yellow precipitate which formed
  5. filtrationwas filtered
  6. washwashed with water
  7. customdried in a vacuum desiccator

Sources & evidence

ORD record
ord-3c2a1ce1cc2444a1a39e3af31aa6891b
Source dataset
uspto-grants-1998_04
Patent number
US05741926

Reaction notes

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