Nitric Acid → HCID 15721804, compound

HRID 2252224Notes

Reaction equation

HRID 2252224 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[C:7](=[O:13])[CH2:6][CH2:5]2.[N+:14]([O-])([OH:16])=[O:15].N([O-])=O.[Na+]>>[OH:1][C:2]1[C:3]([N+:14]([O-:16])=[O:15])=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[C:7](=[O:13])[CH2:6][CH2:5]2

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 147633955-Hydroxy-6-methoxy-2,3-dihydro-1H-inden-1-oneHCID 23668193Sodium Nitrite

Product 1

HCID 15721804HCID 15721804, compound

Procedure

1,4-Dihydroindeno[1,2-c]pyrazoles of general formula (13), wherein X3, R4, R5, and R6 are as defined in formula (I), can be prepared as described in Scheme 3. 5,6-Dimethoxy-1-indanone, purchased from Aldrich Chemical Co., can be treated with sodium cyanide to provide 5-hydroxy-6-methoxy-1-indanone. 5-Hydroxy-6-methoxy-1-indanone can be treated with nitric acid and sodium nitrite to provide 5-hydroxy-6-methoxy-4-nitro-1-indanone. 5-Hydroxy-6-methoxy-4-nitro-1-indanone can be treated with iodomethane and then methodology described in Scheme 2 to provide compounds of general formula (12). Compounds of general formula (12) can be treated with a reducing agent, including iron metal in the presence of acetic acid, to provide amines of general formula (13).

Sources & evidence

ORD record
ord-db3b4896eec840e4b794d2c6e909fa5a
Source dataset
uspto-grants-2008_01
Patent number
US07320986B2

Reaction notes

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