Acetic Acid → HCID 59004233, compound

HRID 2242173Notes

Reaction equation

HRID 2242173 reaction equation
C[N:2]([CH:4]=[C:5]1[C:14](=O)[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH3:16])[CH:12]=2)[O:7][CH2:6]1)C.Cl.[NH:18]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])N.C(O)(=O)C>C(O)C>[CH2:24]([O:23][C:21](=[O:22])[CH2:20][N:18]1[C:14]2[C:13]3[CH:12]=[C:11]([CH3:16])[CH:10]=[CH:9][C:8]=3[O:7][CH2:6][C:5]=2[CH:4]=[N:2]1)[CH3:25]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11593468Acetic acid, 2-hydrazinyl-, ethyl ester, hydrochloride (1:1)HCID 68547419HCID 68547419, compound

Product 1

HCID 59004233HCID 59004233, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of crude 3-Dimethylaminomethylene-6-methyl-chroman-4-one b (1.34 g, 6.16 mmol), ethyl hydrazinoacetate hydrochloride (0.95 g, 6.16 mmol), and a catalytic amount of acetic acid were heated at refluxed in absolute ethanol (10 mL) for overnight. The reaction mixture was concentrated and the residue was purified by column chromatography to get the pure compound c (675 mg; 40% yield, for two steps): LC MS (Method B): 273 (M+1); 1H NMR (400 MHz, CDCl3/TMS):δ 7.37 (s, 1H), 7.02-7.01 (m, 2H), 6.90 (d. J=8.5 Hz, 1H), 5.20 (s, 2H), 5.15 (s, 2H), 4.22 (q, J=7.6 Hz, 2H), 2.36 (s, 3H), 1.22 (t, J=7.6 Hz, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-05364271a9994f478061c08087922708
Source dataset
uspto-grants-2010_03
Patent number
US07671069B2

Reaction notes

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