Sodium Hydroxide → HCID 21717249, compound

HRID 2245541Notes

Reaction equation

HRID 2245541 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:11]#[N:12])[CH:8]=2)[NH:3]1.[OH-:13].[Na+]>S(=O)(=O)(O)O>[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:11]([NH2:12])=[O:13])[CH:8]=2)[NH:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 27733462-Oxo-2,3-dihydro-1H-indole-5-carbonitrile

Product 1

HCID 21717249HCID 21717249, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 2-oxoindoline-5-carbonitrile (2.4 g, 15 mmol) in sulphuric acid (85%, 16 mL) was heated at 80° C. for 6 h and then allowed to reach room temperature over night. The mixture was poured into an ice/water mixture and the pH was adjusted to 5 with an aqueous sodium hydroxide solution (50%). The solid product was collected by filtration, washed with water, and dried in vacuo at 60° C. over night to afford 2.2 g (83% yield): 1H NMR (DMSO-d6, 400 MHz) δ 10.63 (s, 1H), 7.88-7.72 (m, 3H), 7.23-7.11 (br s, 1H), 6.88 (d, J=8 Hz, 1H), 3.56 (s, 2H).

Workup

  1. waitto reach room temperature over night
  2. filtrationThe solid product was collected by filtration
  3. washwashed with water
  4. customdried in vacuo at 60° C. over night
  5. customto afford 2.2 g (83% yield)

Sources & evidence

ORD record
ord-a7ecedd83079498d9b6fed209e910d97
Source dataset
uspto-grants-2010_03
Patent number
US07683067B2

Reaction notes

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