Methylhydrazine → HCID 19917962, compound

HRID 1755879Notes

Reaction equation

CNN.[Cl:4][C:5]1[C:13]2[O:12][C:11]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:10][C:9]=2[C:8]([Cl:26])=[CH:7][C:6]=1[CH2:27][O:28][N:29]1C(=O)C2=CC=CC=C2C1=O>CN(C)C=O>[NH2:29][O:28][CH2:27][C:6]1[CH:7]=[C:8]([Cl:26])[C:9]2[O:10][C:11]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[O:12][C:13]=2[C:5]=1[Cl:4]

Participants

Conditions

Temperature: 0 °C

Procedure

Methylhydrazine (47 mg) (1.02 mmol) are added at 0° C. to a solution of 530 mg (1.02 mmol) of N-[(4,7-dichloro-2,2-diphenyl-1,3-benzodioxol-5-yl)methoxy]phthalimide in 10 ml of absolute dimethylformamide. The mixture is stirred at 0° C. for 1 hour and at room temperature for 4 hours. The solvent is removed in a high vacuum at room temperature and the residue is chromatographed on 30 g of silica gel (0.063-0.2 mm). The product is eluted with dichloromethane/ethanol (19:1 v/v). There are obtained 310 mg of 5-[(aminooxy)methyl]-4,7-dichloro-2,2-diphenyl-1,3-benzodioxol as a colourless oil.

Workup

customThe solvent is removed in a high vacuum at room temperature
customthe residue is chromatographed on 30 g of silica gel (0.063-0.2 mm)
washThe product is eluted with dichloromethane/ethanol (19:1 v/v)

Sources & evidence

ORD record: ord-920bcad435ff429abbef442d46f8300f
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05438052

Reaction notes

Loading…