Hydrochloric Acid → 4-Bromo-2-[(3-ethoxy-3-oxopropanoyl)(propan-2-yl)amino]benzoic acid

HRID 1754557Notes

Reaction equation

HRID 1754557 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([NH:11][CH:12]([CH3:14])[CH3:13])[CH:3]=1.C(N(CC)CC)C.[Cl-].[C:23]([O:29][CH2:30][CH3:31])(=[O:28])[CH2:24][C:25]([O-])=[O:26].Cl>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([N:11]([C:25](=[O:26])[CH2:24][C:23]([O:29][CH2:30][CH3:31])=[O:28])[CH:12]([CH3:14])[CH3:13])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 22464965Ethyl malonate chlorideHCID 248246474-Bromo-2-(isopropylamino)benzoic acid

Product 1

HCID 866798024-Bromo-2-[(3-ethoxy-3-oxopropanoyl)(propan-2-yl)amino]benzoic acidYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-2-(propan-2-ylamino)benzoic acid (6.8 g, 26.64 mmol) in 260 mL of DCM is added triethylamine (4 mL, 31.6 mmol), followed by dropwise addition of ethyl malonate chloride (4.0 mL, 31. mmol). The mixture is stirred for 2 hours at room temperature, and then poured into molar hydrochloric acid solution and extracted with EtOAc. The organic phase is washed with water and with saturated aqueous NaCl solution, dried over Na2SO4 and concentrated to dryness. 7.15 g of a pale yellow solid are obtained (yield: 72%).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase is washed with water and with saturated aqueous NaCl solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-b31ad14ad9db474baa0600e1a45f6bca
Source dataset
uspto-grants-2015_10
Patent number
US09169246B2

Reaction notes

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