Sodium Cyanide → 5-Hydroxy-6-methoxy-2,3-dihydro-1H-inden-1-one

HRID 2252223Notes

Reaction equation

HRID 2252223 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8](=[O:14])[CH2:7][CH2:6]2.[C-]#N.[Na+]>>[OH:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8](=[O:14])[CH2:7][CH2:6]2

Participants

3

Reactant 2

HCID 8929Sodium CyanideHCID 750185,6-Dimethoxy-1-indanone

Product 1

HCID 147633955-Hydroxy-6-methoxy-2,3-dihydro-1H-inden-1-one

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).

Workup

  1. customcan be prepared

Sources & evidence

ORD record
ord-199eeddfa127469494f9181ca6aca5ac
Source dataset
uspto-grants-2008_01
Patent number
US07320986B2

Reaction notes

Loading…