Hydrochloric Acid → HCID 59849175, compound

HRID 604286Notes

Reaction equation

HRID 604286 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[C:20]3[C:16]=2[CH2:17][N:18]([CH3:28])[C:19]3=[O:27])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[OH-].[Na+]>C(O)C.[Fe]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:23]=[CH:22][C:21]([NH2:24])=[C:20]3[C:16]=2[CH2:17][N:18]([CH3:28])[C:19]3=[O:27])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67037850HCID 67037850, compound

Product 1

HCID 59849175HCID 59849175, compoundYield 165.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-(2-methyl-7-nitro-1-oxo-2,3-dihydro-1H-isoindol-4-yloxy)-piperidine-1-carboxylic acid tert-butyl ester (654 mg, 1.0 mmol), iron powder (280 mg, 5.0 mmol), and 1N hydrogen chloride (2 mL, 2.0 mmol) in ethanol (5 mL) is stirred at 80° C. for 1 h under nitrogen atmosphere. After cooling to room temperature, ice and 1N sodium hydroxide are added, the mixture is filtered. The filtrate is extracted with dichloromethane (twice). The combined organic layer is washed with water and then brine, dried over sodium sulfate, filtered and concentrated in vacuo to give 597 mg of 4-(7-amino-2-methyl-1-oxo-2,3-dihydro-1H-isoindol-4-yloxy)-piperidine-1-carboxylic acid tert-butyl ester, which is used for the next reaction without purification.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe mixture is filtered
  3. extractionThe filtrate is extracted with dichloromethane (twice)
  4. washThe combined organic layer is washed with water
  5. dry with materialbrine, dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6a1121292c434da9829d6d70b1834048
Source dataset
uspto-grants-2011_03
Patent number
US07910585B2

Reaction notes

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