Water → HCID 12427497, compound

HRID 1993302Notes

Reaction equation

HRID 1993302 reaction equation
[C:1]([C:9]1[CH:15]=[C:14]2[O:16][CH2:17][O:18][C:13]2=[CH:12][C:10]=1[NH2:11])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[O:20]([C:22]#[N:23])[Na]>CC(O)=O>[CH2:17]1[O:18][C:13]2[CH:12]=[C:10]3[C:9]([C:1]([C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[N:23][C:22](=[O:20])[NH:11]3)=[CH:15][C:14]=2[O:16]1

Participants

5

Reactant 3

HCID 962Water2×HCID 23505677HCID 23505677, compoundHCID 178418852HCID 178418852, compound

Product 1

HCID 12427497HCID 12427497, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of 2-benzoyl-4,5-(methylenedioxy)aniline (200 mg) in AcOH (10 mL) was added water (1 mL) and NaOCN (64 mg) at 10° C. The mixture was stirred at 10° C. for 1 h, then at rt for 2 h. Water (70 mL) was added to the mixture. The resulting yellow solid was collected by filtration, washed with water and 3:2 hexane/EtOAc, recrystallized from DMSO/water to yield the title compound as a yellow solid (104 mg, 47%), mp: 351-354° C. 1H NMR (DMSO-d6): 11.86 (s, 1H), 7.63-7.58 (m, 5H), 6.94 (s, 1H), 6.85 (s, 1H), 6.16 (s, 2H).

Workup

  1. waitat rt for 2 h
  2. filtrationThe resulting yellow solid was collected by filtration
  3. washwashed with water and 3:2 hexane/EtOAc
  4. customrecrystallized from DMSO/water

Sources & evidence

ORD record
ord-f0266a5ee5b24aa48c53d78d180b879c
Source dataset
uspto-grants-2010_01
Patent number
US07652006B2

Reaction notes

Loading…