HCID 67045136, compound → HCID 67044654, compound

HRID 2367085Notes

Reaction equation

HRID 2367085 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:25])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[N:9]2[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:4][C:3]=1[N+:26]([O-])=O>[Pd]>[NH2:26][C:3]1[CH:4]=[C:5]([C:8]2([OH:25])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[N:9]2[CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

3

Reactant 1

HCID 67045136HCID 67045136, compound

Product 1

HCID 67044654HCID 67044654, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 3-(4-amino-3-nitrophenyl)-3-hydroxy-2-(phenylmethyl)-2,3-dihydro-1H-isoindol-1-one (10 g, 26.6 mmol) in a mixture of terahydrofuran-ethyl acetate (1:1, 20 mL) was hydrogenated over 10% Pd—C (100 mg) at 40 psi for 18 h. The catalyst was removed by filtration and the filtrate concentrated in vacuo. The residue was purified by column chromatography (SiO2, hexanes/ethyl acetate) to afford 3-(3,4-diaminophenyl)-3-hydroxy-2-(phenylmethyl)-2,3-dihydro-1H-isoindol-1-one (9.0 g, 98%) as a brown powder. MS (EI) for C21H19N3O2: 368 (MNa+).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue was purified by column chromatography (SiO2, hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-a5bbc0f430d34ea297c853cc32421ccf
Source dataset
uspto-grants-2014_04
Patent number
US08697737B2

Reaction notes

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