Hexane → ethyl N'-{1-[6-benzyloxy-2-hydroxy-3-(5-methyl-7-nitroindan-4-yloxy)phenyl]ethylidene}hydrazinecarboxate

HRID 1766664Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:14]([C:15](=O)[CH3:16])=[C:13]([OH:18])[C:12]([O:19][C:20]2[C:28]([CH3:29])=[CH:27][C:26]([N+:30]([O-:32])=[O:31])=[C:25]3[C:21]=2[CH2:22][CH2:23][CH2:24]3)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:33]([O:37][CH2:38][CH3:39])(=[O:36])[NH:34][NH2:35].CCCCCC>C(O)CC>[CH2:1]([O:8][C:9]1[C:14]([C:15](=[N:35][NH:34][C:33]([O:37][CH2:38][CH3:39])=[O:36])[CH3:16])=[C:13]([OH:18])[C:12]([O:19][C:20]2[C:28]([CH3:29])=[CH:27][C:26]([N+:30]([O-:32])=[O:31])=[C:25]3[C:21]=2[CH2:22][CH2:23][CH2:24]3)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of 1-[6-benzyloxy-2-hydroxy-3-(5-methyl-7-nitroindan-4-yloxy)phenyl]ethanone (1.50 g) in n-propanol (15 mL) was added ethyl carbazate (432 mg). The mixture was stirred under an argon atmosphere at 75° C. overnight and cooled to room temperature. Adding hexane (30 mL), the reaction mixture was stirred for 1 hour. The precipitate was filtrated to give ethyl N′-{1-[6-benzyloxy-2-hydroxy-3-(5-methyl-7-nitroindan-4-yloxy)phenyl]ethylidene}hydrazinecarboxate (1.16 g).

Workup

temperaturecooled to room temperature
filtrationThe precipitate was filtrated

Sources & evidence

ORD record: ord-5714c6000b7b4b63be2a4195baed7260
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07230031B2

Reaction notes

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