HCID 14207583, compound → HCID 14207584, compound

HRID 1252727Notes

Reaction equation

HRID 1252727 reaction equation
[CH2:1]([O:3][C:4]([NH:6][C:7]1[C:17]([CH3:18])=[C:16]([N+:19]([O-])=O)[CH:15]=[C:14]([CH2:22][CH3:23])[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:5])[CH3:2].[H][H]>C(O)C.[Pd]>[NH2:19][C:16]1[CH:15]=[C:14]([CH2:22][CH3:23])[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7]([NH:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:17]=1[CH3:18]

Participants

5

Reactant 2

HCID 14207583HCID 14207583, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14207584HCID 14207584, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of ethyl 2-ethoxycarbonylamino-6-ethyl-3-methyl-4-nitro-benzoate (35 mg) in absolute ethanol (80 ml) was hydrogenated over 10% palladium on charcoal at 50 psi. hydrogen on a Parr hydrogenator for 5 hrs. The catalyst was removed by suction filtration through Celite. The filtrate was evaporated to give an oil which was further purified by thick layer chromatography (30% ethyl acetate: pet. ether 30-60) to give ethyl 4-amino-2-ethoxycarbonylamino-6-ethyl-3-methyl-benzoate as a white solid (30 mg). IR (CH2Cl2): 3340, 1700 (br.), 1600 cm-1. H-NMR (CD3OD): 1.00-1.50 (overlapping peaks [3t], 9H, CH3CH2, 2CH3CH2O), 2.00 (s, 3H, CH3), 2.60 (q, 2H, CH2Ar), 4.15 (q, 2H, CH2), 4.30 (q, 2H, CH2), 6.60 (s, 1 H, ArH).

Workup

  1. customThe catalyst was removed by suction filtration through Celite
  2. customThe filtrate was evaporated
  3. customto give an oil which
  4. customwas further purified by thick layer chromatography (30% ethyl acetate: pet. ether 30-60)

Sources & evidence

ORD record
ord-4832d2684e0f404dbda441360da5cff3
Source dataset
uspto-grants-1988_05
Patent number
US04745116

Reaction notes

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