Acetyl chloride → Methyl 3-(3,4-dihydroxyphenyl)-2-hydrazinyl-2-methylpropanoate

HRID 2212438Notes

Reaction equation

HRID 2212438 reaction equation
[CH3:1][C@@:2]([NH:15][NH2:16])([C:12]([OH:14])=[O:13])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([OH:11])=[C:8]([OH:10])[CH:9]=1.[C:17](Cl)(=O)C>CO>[OH:10][C:8]1[CH:9]=[C:4]([CH2:3][C:2]([NH:15][NH2:16])([CH3:1])[C:12]([O:14][CH3:17])=[O:13])[CH:5]=[CH:6][C:7]=1[OH:11]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 34359Carbidopa

Product 1

HCID 13589972Methyl 3-(3,4-dihydroxyphenyl)-2-hydrazinyl-2-methylpropanoateYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of carbidopa (226 mg, 1 mmol) in anhydrous methanol (20 mL), was added acetyl chloride (1 mL) at 0° C. The mixture was stirred at 65° C. in a pressure vessel for 4 h. Removal of solvent yielded 270 mg (99%) of the title compound as its hydrochloride salt. 1H NMR (CD3OD, 400 MHz): 1.46 (s, 3H), 2.86 (dd, 2H), 3.78 (s, 3H), 6.45 (dd, J=8 Hz, J=2 Hz), 6.56 (d, J=2.4 Hz), 6.69 (d, J=8.4 Hz). MS (ESI) m/z 241.15 (M+H+).

Workup

  1. customRemoval of solvent

Sources & evidence

ORD record
ord-0b0f89390a17439fa153a63a78b859a8
Source dataset
uspto-grants-2006_09
Patent number
US07101912B2

Reaction notes

Loading…