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

HRID 330966Notes

Reaction equation

HRID 330966 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-46e2b27df68145f6bc3dffc66820f7e3
Source dataset
uspto-grants-2014_11
Patent number
US08877743B2

Reaction notes

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