Dichloromethane → 1H-Imidazole-1-carboxylic acid, 4-[(aminooxy)methyl]-, 1,1-dimethylethyl ester

HRID 2400670Notes

Reaction equation

HRID 2400670 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[O:12][CH2:13][C:14]1[N:15]=[CH:16][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:18]=1.C(Cl)Cl.O.NN>C(O)C>[NH2:3][O:12][CH2:13][C:14]1[N:15]=[CH:16][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:18]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24654Hydrazine hydrate (1:1)HCID 86693986HCID 86693986, compound

Product 1

HCID 866939871H-Imidazole-1-carboxylic acid, 4-[(aminooxy)methyl]-, 1,1-dimethylethyl esterYield 51%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of tert-butyl 4-{[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]methyl}-1H-imidazole-1-carboxylate 121 (1.72 g, 5.00 mmol) in a solution of DCM (20 mL) and ethanol (4 mL) was added hydrazine hydrate (0.287 mL, 5.00 mmol) at room temperature. The mixture was stirred at room temperature overnight, filtered and concentrated to provide a residue which was washed with ether and methanol to give 122 (0.54 g, 51%) as a white solid.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customto provide a residue which
  4. washwas washed with ether and methanol

Sources & evidence

ORD record
ord-88a1df0d5a2f41eabca964c64c51e302
Source dataset
uspto-grants-2014_08
Patent number
US08796257B2

Reaction notes

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