Bromoacetyl bromide → HCID 18929195, compound

HRID 1599820Notes

Reaction equation

HRID 1599820 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Br:12][CH2:13][C:14](Br)=[O:15]>CN(C=O)C.O1CCOCC1>[Br:12][CH2:13][C:14]([NH:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])=[O:15]

Participants

5

Reactant 2

HCID 61147Bromoacetyl bromideHCID 1645925-Hydroxyanthranilic acid

Product 1

HCID 18929195HCID 18929195, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-amino-5-hydroxybenzoic acid (6.1 g, 0.04 mol) in anhydrous DMF (20 mL) and anhydrous dioxane (20 mL) was added, dropwise, bromoacetyl bromide (8.0 g, 3.5 mL, 100 mol %) while keeping the internal temperature between 0° C. and 5° C. After the addition was completed (~20 min), the ice-bath was removed and the mixture was stirred for 20 h at rt. The reaction mixture was cooled in an ice-bath, water was added (100 mL), and then the mixture was poured into ice-water. The light precipitate which formed was filtered and then dried in a vacuum oven for 20 h at 40°-45° C., giving 7.8 g (72%) of the title compound: mp 213°-215.3° C.; 1H NMR (DMSO-d6) δ13.56 (bs, 1H, OH), 11.19 (s, 1H, NH), 9.68 (s, 1H, OH), 8.19 (d, 1H, J=8.8), 7.36 (d, 1H, J=3.2), 7.01 (dd, 1H, J=3.2, J=9.2), 4.19 (s, 2H); 13C NMR (DMSO-d6) δ168.88, 164.32, 153.08, 131.69, 122.21, 120.79, 119.00, 116.60, 30.66; MS (EI, m/z) 273 (M+), 275 (M+2+). HRMS (EI) calcd for C9H8NO4Br 272.9637, found 272.9634.

Workup

  1. customthe internal temperature between 0° C. and 5° C
  2. additionAfter the addition
  3. custom(~20 min)
  4. customthe ice-bath was removed
  5. temperatureThe reaction mixture was cooled in an ice-bath
  6. additionwater was added (100 mL)
  7. additionthe mixture was poured into ice-water
  8. customThe light precipitate which formed
  9. filtrationwas filtered
  10. customdried in a vacuum oven for 20 h at 40°-45° C.

Sources & evidence

ORD record
ord-66d5a513a1ad4e0481e974a585f860a1
Source dataset
uspto-grants-1998_04
Patent number
US05741926

Reaction notes

Loading…