2-Bromoaniline → HCID 18929248, compound

HRID 1599843Notes

Reaction equation

HRID 1599843 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9])=[O:4].[Br:16][C:17]1[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=1[NH2:19]>CN(C=O)C>[Br:16][C:17]1[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=1[NH:19][CH2:2][C:3]([NH:5][C:6]1[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9])=[O:4]

Participants

4

Reactant 2

HCID 119922-BromoanilineHCID 4062738Methyl 2-((Bromoacetyl)Amino)Benzoate(WX618077)

Product 1

HCID 18929248HCID 18929248, compoundYield 30.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 2-((bromoacetyl)amino)benzoate (2.0 g, 7.35 mmol) and 2-bromoaniline (3.16 g, 18.4 mmol) in anhydrous DMF (30 mL) was heated to 90°-100° C. overnight with stirring under N2. The solution was cooled, poured into 500 mL of ice-water, and then extracted with 3×50 mL of ethyl acetate. The layers were separated and the organic layer was dried (MgSO4), filtered, and then concentrated. Purification by chromatography, eluting with hexane-ethyl acetate (3:1), afforded 0.81 g (30%) of the title compound, mp 89°-91° C.: 1H NMR (DMSO-d6) δ11.19 (s, 1H), 8.52 (dd, J=8.4, J=0.8, 1H), 7.90 (dd, J=8.0, J=1.6, 1H), 7.62 (ddd, J=8.8, J=7.6, J=1.6, 1H), 7.47 (dd, J=8.0, J=1.6, 1H), 7.20-7.14 (m, 2H), 6.60 (ddd, J=8.4, J=8.0, J=1.2, 1H), 6.53 (dd, J=8.4, J=1.6, 1H), 6.06 (bt, J=5.6, 1H), 4.00 (d, J=5.6, 2H), 3.73 (s, 3H); 13C NMR (DMSO-d6) δ169.70, 167.01, 144.53, 139.32, 134.16, 132.36, 130.68, 128.67, 123.21, 120.40, 118.35, 116.66, 111.51, 109.04, 52.26, 48.47; MS (El, m/z) 363 (M+). Anal. Calcd for C16H15N2O3Br: C, 52.91; H, 4.16; N, 7.71. Found: C, 52.22; H, 4.05; N, 7.40.

Workup

  1. temperatureThe solution was cooled
  2. extractionextracted with 3×50 mL of ethyl acetate
  3. customThe layers were separated
  4. dry with materialthe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by chromatography
  8. washeluting with hexane-ethyl acetate (3:1)

Sources & evidence

ORD record
ord-ca3f4192232e4ccf9dd390d8e79c1b47
Source dataset
uspto-grants-1998_04
Patent number
US05741926

Reaction notes

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