Water → (S)-Methyl 2-(6-(4-aminophenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

HRID 403700Notes

Reaction equation

HRID 403700 reaction equation
[CH3:1][CH:2]([CH3:27])[C@H:3]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][C:12]([C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=3)=[CH:13][CH:14]=2)[C:9]1=[O:26])[C:4]([O:6][CH3:7])=[O:5].[Cl-].[NH4+].C1COCC1.O>CCO.C(OCC)(=O)C.[Fe]>[NH2:23][C:20]1[CH:19]=[CH:18][C:17]([C:12]2[CH:11]=[C:10]3[C:15]([CH2:16][N:8]([C@@H:3]([CH:2]([CH3:27])[CH3:1])[C:4]([O:6][CH3:7])=[O:5])[C:9]3=[O:26])=[CH:14][CH:13]=2)=[CH:22][CH:21]=1

Participants

8

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 131731440(S)-Methyl 3-methyl-2-(6-(4-nitrophenyl)-1-oxoisoindolin-2-yl)butanoate

Product 1

HCID 131731441(S)-Methyl 2-(6-(4-aminophenyl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound of example 5 (0.9 g, 0.00244 mol), iron (0.32 g, 0.0057 mol) and ammonium chloride (0.551 g, 0.0103 mol) were taken in EtOH:THF:H2O (15.5 mL, 9:4.5:2.25). The reaction mixture was refluxed for about 16 h. After completion of the reaction, the reaction mixture was filtered through celite. The filtrate was concentrated to obtain a solid residue which was dissolved in ethyl acetate and washed with water and brine, dried over anhydrous sodium sulfate and concentrated to obtain a crude product, which was purified by column chromatography (silicagel, 30% ethyl acetate in petroleum ether).

Workup

  1. temperatureThe reaction mixture was refluxed for about 16 h
  2. customAfter completion of the reaction
  3. filtrationthe reaction mixture was filtered through celite
  4. concentrationThe filtrate was concentrated
  5. customto obtain a solid residue which
  6. washwashed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c716bd7ada7b40d8ae855d48f83b9132
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Reaction notes

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