Benzenepropanoic acid, 3-bromo-3-oxo-, ethyl ester → HCID 71284241, compound

HRID 717535Notes

Reaction equation

HRID 717535 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH2:11])[C:7]([NH2:10])=[CH:8][CH:9]=1)([O-:3])=[O:2].[Br:12][C:13]1[CH:14]=[C:15]([C:19](=O)[CH2:20][C:21](OCC)=[O:22])[CH:16]=[CH:17][CH:18]=1>C(O)(=O)C>[Br:12][C:13]1[CH:14]=[C:15]([C:19]2[CH2:20][C:21](=[O:22])[NH:11][C:6]3[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:9]=[CH:8][C:7]=3[N:10]=2)[CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 179368Benzenepropanoic acid, 3-bromo-3-oxo-, ethyl esterHCID 51117914-Nitro-1,2-phenylenediamine

Product 1

HCID 71284241HCID 71284241, compoundYield 39.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

To a stirred solution of 4-nitrobenzene-1,2-diamine 2 (1.0 g, 6.53 mmol) in acetic acid (20 mL) was added ethyl 3-(3-bromophenyl)-3-oxopropanoate 1 (1.75 g, 6.53 mmol) at RT under inert atmosphere. The resulting reaction mixture was heated to 110° C. and stirred for 12 h. After complete consumption of the starting material (by TLC), the reaction mixture was cooled to RT and diluted with water (100 mL) and extracted with EtOAc (3×50 mL). The combined organic extracts were dried over anhydrous Na2SO4 and concentrated under reduced pressure and the obtained crude was purified by silica gel column chromatography (eluent: 25% EtOAc/Hexane) to afford compound 3 (0.91 g, 39.5%) as yellow solid. 1H NMR (500 MHz, DMSO-d6): δ 10.91 (bs, 1H), 8.25 (s, 1H), 8.09-8.01 (m, 3H), 7.82 (d, J=6.4 Hz, 1H), 7.68 (d, J=7.6 Hz, 1H), 7.57-7.48 (m, 1H), 3.67 (s, 2H). MS (ESI): 361 [M+1]+

Workup

  1. customThe resulting reaction mixture
  2. customAfter complete consumption of the starting material (by TLC)
  3. temperaturethe reaction mixture was cooled to RT
  4. additiondiluted with water (100 mL)
  5. extractionextracted with EtOAc (3×50 mL)
  6. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customthe obtained crude
  9. customwas purified by silica gel column chromatography (eluent: 25% EtOAc/Hexane)

Sources & evidence

ORD record
ord-e24cf15447444fef94a73423e83a53ac
Source dataset
uspto-grants-2015_11
Patent number
US09193710B2

Reaction notes

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