HCID 59017475, compound → HCID 69511218, compound

HRID 969666Notes

Reaction equation

HRID 969666 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:13][C:14](=[O:24])[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N+:21]([O-:23])=[O:22])[CH:11]=2)[C:6]([CH3:26])([CH3:25])[CH2:5]1)(=O)C>CCO.Cl>[CH3:25][C:6]1([CH3:26])[C:7]2[C:12](=[CH:11][C:10]([NH:13][C:14](=[O:24])[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N+:21]([O-:23])=[O:22])=[CH:9][CH:8]=2)[NH:4][CH2:5]1

Participants

4

Reactant 1

HCID 59017475HCID 59017475, compound

Product 1

HCID 69511218HCID 69511218, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

N-(1-Acetyl-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-2-nitro-benzamide (Step A) (3.0 g, 8.5 mmol) was dissolved in EtOH (80 mL) in the presence of HCl (1 N, 18 mL). The solution was heated to 70° C. overnight. Solvent was removed in vacuo and the residue was partitioned in EtOAc and a solution of NaHCO3 (aq. sat.). A yellow precipitate formed in the organic layer. After separation from the aqueous layer, the organic layer was filtered to give a solid. The filtrate was concentrated to give a second batch. The combined batches were used without further purification.

Workup

  1. customSolvent was removed in vacuo
  2. customthe residue was partitioned in EtOAc
  3. customA yellow precipitate formed in the organic layer
  4. customAfter separation from the aqueous layer
  5. filtrationthe organic layer was filtered
  6. customto give a solid
  7. concentrationThe filtrate was concentrated
  8. customto give a second batch
  9. customThe combined batches were used without further purification

Sources & evidence

ORD record
ord-f86df2a3720e4b25b0fede565a9b7275
Source dataset
uspto-grants-2007_12
Patent number
US07307088B2

Reaction notes

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