Aniline → HCID 11000106, compound

HRID 1490312Notes

Reaction equation

HRID 1490312 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9])=[O:4].[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-].[K+]>CN(C=O)C>[C:16]1([NH:15][CH2:2][C:3]([NH:5][C:6]2[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=2[C:8]([OH:10])=[O:9])=[O:4])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 14797Potassium HydroxideHCID 10611190HCID 10611190, compound

Product 1

HCID 11000106HCID 11000106, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(N-Bromoacetylamino)benzoic acid from Example 79 (5.0 g, 19.37 mmol), aniline (4.51 g, 4.41 mL, 48.4 mmol) and anhyd DMF (50 mL) was heated in an oil bath at 85° C. for 4.5 h. The reaction mixture was cooled and poured into ice-water (500 mL). A solution of 5% KOH (100 mL) was added to dissolve the milky white suspension and the resulting homogenous solution was extracted with CH2Cl2 (200 mL, 2×100 mL). The combined CH2Cl2 extract was set aside and the aqueous layer was acidified to pH=3 (pH meter) with 5% HBr. The resulting precipitate was washed with 5% HBr solution and water, and then dried in a vacuum oven at 50° C. for 2 days, yielding 4.74 g (90.6%) of a white powder, mp 192.4°-192.8° C. (sealed tube); 1H NMR (DMSO-d6) 13.41 (bs, 1H), 12.01 (s, 1H), 8.72 (d, J=8.4, 1H), 7.93 (dd, J=7.6, J=1.6, 1H), 7.59 (dt, J=8.8, J=1.6, 1H), 7.15-7.05 (m, 3H), 6.63-6.45 (m, 4H); 3.83 (s, 2H); 13C NMR (DMSO-d6) δ 170.85, 169.01, 148.11, 140.56, 134.13, 131.10, 128.94, 122.63, 119.38, 117.10, 115.96, 112.40, 48.93; MS (EI, m/z) 270.1 (M+) .

Workup

  1. temperatureThe reaction mixture was cooled
  2. dissolutionto dissolve the milky white suspension
  3. extractionthe resulting homogenous solution was extracted with CH2Cl2 (200 mL, 2×100 mL)
  4. extractionThe combined CH2Cl2 extract
  5. washThe resulting precipitate was washed with 5% HBr solution and water
  6. customdried in a vacuum oven at 50° C. for 2 days
  7. customyielding

Sources & evidence

ORD record
ord-d76e89f6df224ed69efe55ba56707edb
Source dataset
uspto-grants-1997_10
Patent number
US05681958

Reaction notes

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