Formic Acid → HCID 10361732, compound

HRID 1453996Notes

Reaction equation

HRID 1453996 reaction equation
N[C:2]1[O:3][C:4]2[C:9]([CH:10]([C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=3)[C:11]=1[C:12]#[N:13])=[CH:8][CH:7]=[C:6]([O:26][CH3:27])[CH:5]=2.C(O)=[O:29]>>[C:12]([CH:11]1[CH:10]([C:14]2[CH:15]=[C:16]([O:24][CH3:25])[C:17]([O:22][CH3:23])=[C:18]([O:20][CH3:21])[CH:19]=2)[C:9]2[C:4](=[CH:5][C:6]([O:26][CH3:27])=[CH:7][CH:8]=2)[O:3][C:2]1=[O:29])#[N:13]

Participants

3

Reactant 2

HCID 284Formic AcidHCID 10109587HCID 10109587, compound

Product 1

HCID 10361732HCID 10361732, compound

Procedure

2-Amino-3-cyano-7-methoxy-4-(3,4,5-trimethoxyphenyl)-4H-chromene (260 mg, 0.7 mmol) was dissolved into approximately 5 mL of formic acid. The obtained white suspension was stirred approximately 1 h at room temperature until it solubilized. The solvent was evaporated. The residue was dissolved into ethyl acetate (20 mL), washed with sodium bicarbonate saturated solution (2×20 mL), brine (20 mL), dried over sodium sulfate and concentrated to give approximately 210 mg of a mixture of diastereoisomers. 1H NMR (CDCl3): 7.12 (d, J=8.2 Hz, 0.5H), 6.82-6.67 (m, 2.5H), 6.41 (s, 1H), 6.37 (s, 1H), 4.48-4.43 (m, 1H), 4.25-4.02 (m, 1H), 3.86-3.78 (4s, 12H)

Workup

  1. customThe solvent was evaporated
  2. dissolutionThe residue was dissolved into ethyl acetate (20 mL)
  3. washwashed with sodium bicarbonate saturated solution (2×20 mL), brine (20 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-182d59854c6546a0af88e9c3b29d6abc
Source dataset
uspto-grants-2009_01
Patent number
US07476741B2

Reaction notes

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