Sodium Hydroxide → 5,6-Diamino-3,3-dimethyl-1-pent-2-ynyl-1,3-dihydro-indol-2-one

HRID 2235424Notes

Reaction equation

HRID 2235424 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-])=O)[N:7]([CH2:14][C:15]#[C:16][CH2:17][CH3:18])[C:6](=[O:19])[C:5]2([CH3:21])[CH3:20].[OH-].[Na+]>C1COCC1.Cl>[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH2:11])[N:7]([CH2:14][C:15]#[C:16][CH2:17][CH3:18])[C:6](=[O:19])[C:5]2([CH3:20])[CH3:21]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 593009855-Amino-3,3-dimethyl-6-nitro-1-(pent-2-ynyl)-1,3-dihydro-indol-2-one

Product 1

HCID 593009835,6-Diamino-3,3-dimethyl-1-pent-2-ynyl-1,3-dihydro-indol-2-oneYield 65.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of A7 (0.87 g) in THF (17 ml) is added a solution of SnCl2 dihydrate (2.73 g; 12.1 mmol) in hydrochloric acid (50 ml; 1 N) dropwise. The reaction mixture is stirred at RT for 3 h. After completion 1 N NaOH (until pH 12) is added and the mixture is extracted with CH2Cl2 (2×75 ml). The combined organic layer is washed with brine, dried over MgSO4 and evaporated to give 5,6-diamino-3,3-dimethyl-1-pent-2-ynyl-1,3-dihydro-indol-2-one (0.51 g) which is used without further purification.

Workup

  1. extractionthe mixture is extracted with CH2Cl2 (2×75 ml)
  2. washThe combined organic layer is washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-161d4941cd614571b95da191635e357e
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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