Hydrazine hydrate (1:1) → 3-(2,5-Dichlorophenyl)-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]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[Cl:26])=O)(=O)OC.O.[NH2:28][NH2:29]>>[Cl:26][C:20]1[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:19]=1[C:17]1[N:28]=[N:29][C:2]2[CH:1]3[CH2:7][CH:4]([C:3]=2[CH:16]=1)[CH2:5][CH2:6]3

Participants

Reactant 3

HCID 24654Hydrazine hydrate (1:1)

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

HCID 86252874HCID 86252874, compound

Product 1

HCID 673636623-(2,5-Dichlorophenyl)-5,6,7,8-tetrahydro-5,8-methanocinnoline

Procedure

yellow crystalline solid. MS (ESI): 291.0 (MH+). Prepared from bicyclo[2.2.1]heptane-2,3-dione, [2-(2,5-Dichloro-phenyl)-2-oxo-ethyl]-phosphonic acid dimethyl ester, hydrazine monohydrate.

Sources & evidence

ORD record: ord-2b6083e1338843cb9d1f384a40fd6688
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07678795B2

Reaction notes

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