Acetic Acid → HCID 11537306, compound

HRID 2235395Notes

Reaction equation

HRID 2235395 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]([NH:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][C:20]=2[N+:21]([O-])=O)[N:17]([CH3:24])[C:16](=[O:25])[C:15]3([CH3:27])[CH3:26])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:28](O)(=O)C>[Pd]>[CH3:24][N:17]1[C:18]2[CH:19]=[C:20]3[N:21]=[C:9]([CH2:8][CH2:7][C:1]4[CH:6]=[CH:5][C:4]([CH3:28])=[CH:3][CH:2]=4)[NH:11][C:12]3=[CH:13][C:14]=2[C:15]([CH3:27])([CH3:26])[C:16]1=[O:25]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 23092682HCID 23092682, compound

Product 1

HCID 11537306HCID 11537306, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 3-phenyl-N-(1,3,3-trimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-propionamide (532 mg) in acetic acid (8 ml) is hydrogenated at 2-4 bar at RT using Pd/C (10%, 80 mg), where upon ring closure occurs. After evaporation of the solvent the residue is taken-up in NaOH solution (2 N) and extracted with EtOAc (2×20 ml). The combined organic layer is washed with brine, dried over Na2SO4 and evaporated. The residual material is triturated with acetone to give the desired compound (466 mg).

Workup

  1. customis hydrogenated at 2-4 bar at RT
  2. customAfter evaporation of the solvent the residue
  3. extractionextracted with EtOAc (2×20 ml)
  4. washThe combined organic layer is washed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe residual material is triturated with acetone

Sources & evidence

ORD record
ord-921da65f391b4004896a76773a6a8401
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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