[2-Nitro-4-(3-nitro-benzoyl)-phenyl]-acetic acid ethyl ester → [2-Amino-4-(3-amino-benzoyl)-phenyl]-acetic acid ethyl ester

HRID 2352891Notes

Reaction equation

HRID 2352891 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:22])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-])=O)[CH:14]=2)=[CH:8][C:7]=1[N+:23]([O-])=O)[CH3:2]>C(O)C>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:22])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([NH2:19])[CH:14]=2)=[CH:8][C:7]=1[NH2:23])[CH3:2]

Participants

3

Reactant 1

HCID 86610408[2-Nitro-4-(3-nitro-benzoyl)-phenyl]-acetic acid ethyl ester

Product 1

HCID 68699186[2-Amino-4-(3-amino-benzoyl)-phenyl]-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 2 L metal reactor was charged with [2-Nitro-4-(3-nitro-benzoyl)-phenyl]-acetic acid ethyl ester (65 g, 181.4 mmol) in ethanol (1.3 L) was added Pt(IV)O2 (6.5 g). The reactor was evacuated, purged with N2(g) then filled with H2(g) (15 psi). The temperature of the reaction was controlled with a H2O coiled condenser and the maximum allowable temperature was 26° C. After 1 h and 15 min, the reaction was determined to be complete by thin layer chromatographic analysis (TLC) (Hexanes/EtOAc 1:1). The TLC was viewed with short wavelength UV and I2 stain. At the end of the reaction, the reactor was evacuated and purged with N2(g). The reaction was filtered through celite and the celite was washed with THF (1 L). The filtrates were concentrated and the solids were dried in a vacuum oven under 28 mmHg at 45° C. to afford [2-Amino-4-(3-amino-benzoyl)-phenyl]-acetic acid ethyl ester in quantitative yield (54 g, 181.0 mmol).

Workup

  1. customThe reactor was evacuated
  2. custompurged with N2(g)
  3. additionthen filled with H2(g) (15 psi)
  4. customThe temperature of the reaction was controlled with a H2O coiled condenser
  5. customwas 26° C
  6. custom15 min
  7. customAt the end of the reaction
  8. customthe reactor was evacuated
  9. custompurged with N2(g)
  10. filtrationThe reaction was filtered through celite
  11. washthe celite was washed with THF (1 L)
  12. concentrationThe filtrates were concentrated
  13. customthe solids were dried in a vacuum oven under 28 mmHg at 45° C.

Sources & evidence

ORD record
ord-7779925ce1b44da2bd49266edccc47d5
Source dataset
uspto-grants-2010_07
Patent number
US07749530B2

Reaction notes

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