Hydrazine hydrate (1:1) → 3-(4-Fluoro-2-methylphenyl)-5,6,7,8-tetrahydro-5,8-methanocinnoline

Reaction equation

[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[C:3](=O)[C:2]2=O.COP([CH2:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=1[CH3:26])=O)(=O)OC.O.[NH2:28][NH2:29]>>[F:25][C:22]1[CH:23]=[CH:24][C:19]([C:17]2[N:28]=[N:29][C:2]3[CH:1]4[CH2:7][CH:4]([C:3]=3[CH:16]=2)[CH2:5][CH2:6]4)=[C:20]([CH3:26])[CH:21]=1

Participants

Reactant 3

HCID 24654Hydrazine hydrate (1:1)

HCID 138696Bicyclo(2.2.1)heptane-2,3-dione

HCID 86609925HCID 86609925, compound

Product 1

HCID 673633723-(4-Fluoro-2-methylphenyl)-5,6,7,8-tetrahydro-5,8-methanocinnoline

Procedure

yellow oil. MS (EI): 254.2 (M+). Prepared from bicyclo[2.2.1]heptane-2,3-dione, [2-(4-Fluoro-2-methyl-phenyl)-2-oxo-ethyl]-phosphonic acid dimethyl ester, hydrazine monohydrate.

Sources & evidence

ORD record: ord-d51f218bfe5746e3a2dba08db20049dd
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07678795B2

Reaction notes

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