Hydrochloric Acid → HCID 12221869, compound

HRID 1744441Notes

Reaction equation

HRID 1744441 reaction equation
[C:1]([C:3]1[C:4](=N)[O:5][C:6]2[C:11]([C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)#[N:2].Cl.C[OH:22]>>[C:1]([C:3]1[C:4](=[O:22])[O:5][C:6]2[C:11]([C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)#[N:2]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 22136803HCID 22136803, compound

Product 1

HCID 12221869HCID 12221869, compoundYield 39%

Procedure

To a solution of 3-cyano-2-imino-4-phenyl-2H-chromene (90 mg, 0.37 mmol) in methanol (10 mL) was added 37% HCl (0.037 ml, 0.37 mmol). The mixture was stirred at room temperature for 2 h. The solvent was evaporated and the residue was purified by chromatography on silica gel with ethyl acetate and hexane (1:2) as eluant, yielding 35 mg (39%) of the title compound. 1H NMR (CDCl3): 7.80-7.74 (m, 1H), 7.66-7.60 (m, 3H), 7.57-7.54 (m, 1H), 7.47-7.44 (m, 2H), 7.41-7.32 (m, 2H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by chromatography on silica gel with ethyl acetate and hexane (1:2) as eluant

Sources & evidence

ORD record
ord-9318e381d3fb4e1698a62705374c661e
Source dataset
uspto-grants-2006_03
Patent number
US07015328B2

Reaction notes

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