HCID 11139347, compound → HCID 69159126, compound

HRID 967398Notes

Reaction equation

HRID 967398 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[N+:13]([O-])=O)[CH3:2]>C1C=CC=CC=1.O=[Pt]=O>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[NH2:13])[CH3:2]

Participants

4

Reactant 1

HCID 11139347HCID 11139347, compound

Product 1

HCID 69159126HCID 69159126, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 241BenzeneSolvent

Procedure

(5-Chloro-2-nitro-phenyl)-acetic acid ethyl ester (5.9 g, 24.2 mmol) in benzene (125 mL) containing PtO2 (500 mg) was placed on a Parr hydrogenator at 40 psi H2. After 18 h the mixture was filtered through celite and evaporated to give a clear brown liquid. The liquid was purified (silica, 25% EtOAc/hexanes) to give 3.3 g (64%) of a clear golden liquid. TLC (silica, 25% EtOAc/hexanes): Rf=0.30. MS (electrospray): exact mass calculated for C10H12ClNO2, 213.06. m/z found, 214.1 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.20-7.10 (m, 2H), 6.78 (d, J=8.3 Hz, 1H), 4.26 (q, J=7.2, 2H), 1.18 (t, J=7.1 Hz, 3H).

Workup

  1. filtrationAfter 18 h the mixture was filtered through celite
  2. customevaporated
  3. customto give a clear brown liquid
  4. customThe liquid was purified (silica, 25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-5126b9189ae24738885f16a81abce010
Source dataset
uspto-grants-2005_10
Patent number
US06953793B2

Reaction notes

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