Ethyl diazoacetate → 4,6,7,8-tetrahydro-1,3-dimethyl-5(1H)-cycloheptapyrazolone

HRID 569900Notes

Reaction equation

[CH3:1][N:2]1[C:10]2[CH2:9][CH2:8][CH2:7][C:6](=[O:11])[C:5]=2[C:4]([CH3:12])=[N:3]1.[N+](=[CH:15]C(OCC)=O)=[N-]>>[CH3:1][N:2]1[C:10]2[CH2:9][CH2:8][CH2:7][C:6](=[O:11])[CH2:15][C:5]=2[C:4]([CH3:12])=[N:3]1

Participants

Reactant 2

HCID 12192Ethyl diazoacetate

HCID 141266791,3-dimethyl-4,5,6,7-tetrahydro-1H-indazol-4-one

Product 1

HCID 201465864,6,7,8-tetrahydro-1,3-dimethyl-5(1H)-cycloheptapyrazolone

Procedure

1,5,6,7-Tetrahydro-1,3-dimethyl-4H-indazol-4-one is reacted with ethyl diazoacetate according to the procedure described in Example 3 to give 4,6,7,8-tetrahydro-1,3-dimethyl-5(1H)-cycloheptapyrazolone. This is reacted with N,N-dimethylformamide dimethyl acetal according to the procedure described in the first paragraph of Example 6 to give 4-(dimethylaminomethylene)-4,6,7,8-tetrahydro-1,3-dimethyl-5(1H)-cycloheptapyrazolone. The dimethylaminomethylene compound is then reacted with hydrazine according to the procedure described in Example 7 to give 4,5,6,7-tetrahydro-1,3-dimethyl-3H-cyclohepta[1,2-c:4,3-c']dipyrazole.

Sources & evidence

ORD record: ord-4035628d196a4d5886609e1c3299a226
Source dataset: uspto-grants-1988_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04734429

Reaction notes

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