Acetic Acid → HCID 86758393, compound

HRID 2302276Notes

Reaction equation

HRID 2302276 reaction equation
[C:1]([O:5][C:6]([NH:8][NH:9][CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][C:13](=[O:21])[O:12]1.C(O)(=O)C>CCOC(C)=O>[OH:12][CH2:11][C:20]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:14][C:13]([N:9]([CH3:10])[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[O:21]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 780921,4-dihydro-3H-2-benzopyran-3-oneHCID 15671306N'-methyl(tert-butoxy)carbohydrazide

Product 1

HCID 86758393HCID 86758393, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

N-(t-Butoxycarbonyl)-N′-methylhydrazine (100 mmol) (Lenman, et al., J. Chem. Soc. Perkin Trans., 1997, 16, 2297-2312; Dutta, et al., J. Chem. Soc. Perkin Trans., 1986, 1655-1664) was added to 3-isochromanone (7.4 g, 50 mmol) (Cheng, et al., J. Heterocyclic Chem., 1995, 32, 73) in a sealed tube followed by 0.2 mL of acetic acid and heated for 12 h at 100° C. The reaction mixture was diluted with EtOAc (100 mL), washed with water (50 mL),1 M HCl (50 mL), brine (50 mL) and dried (Na2SO4). The desired alcohol 2-[2-[2-(Hydroxymethyl)phenyl]-1-oxoethyl]-2-methylhydrazinecarboxylic acid, 1,1-dimethylethyl ester was purified by flash chromatography (silica) using 50% EtOAc in hexane as eluent. MS (ESI) 295 (M+H).

Workup

  1. washwashed with water (50 mL),1 M HCl (50 mL), brine (50 mL)
  2. dry with materialdried (Na2SO4)
  3. customThe desired alcohol 2-[2-[2-(Hydroxymethyl)phenyl]-1-oxoethyl]-2-methylhydrazinecarboxylic acid, 1,1-dimethylethyl ester was purified by flash chromatography (silica)

Sources & evidence

ORD record
ord-51fed0c6f1b849978a8940cef17adbd9
Source dataset
uspto-grants-2002_08
Patent number
US06432944B1

Reaction notes

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