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

HRID 1053388Notes

Reaction equation

HRID 1053388 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-fa172fca325a448684a4f21c2a224add
Source dataset
uspto-grants-2016_07
Patent number
US09393239B2

Reaction notes

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