Acetic Acid → 2-[4-(7-Methoxy-6-methyl-indan-4-ylmethyl)-3,5-dimethyl-pyrazol-1-yl]-ethanol

HRID 389309Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:4]([CH3:20])=[CH:5][C:6]([CH2:12][CH:13]([C:17](=O)[CH3:18])[C:14](=O)[CH3:15])=[C:7]2[C:11]=1[CH2:10][CH2:9][CH2:8]2.[NH:21]([CH2:23][CH2:24][OH:25])[NH2:22].C(O)(=O)C>C(O)C.C(OCC)C>[CH3:1][O:2][C:3]1[C:4]([CH3:20])=[CH:5][C:6]([CH2:12][C:13]2[C:17]([CH3:18])=[N:22][N:21]([CH2:23][CH2:24][OH:25])[C:14]=2[CH3:15])=[C:7]2[C:11]=1[CH2:10][CH2:9][CH2:8]2

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of 3-(7-Methoxy-6-methyl-indan-4-ylmethyl)-pentane-2,4-dione (1.0 gm 0.0036 mole) in Ethanol (15 ml), a solution of 2-Hydrazino-ethanol (0.33 gm, 0.0043 mole) in Ethanol (5 ml) was added at 25-30° C. and reaction mixture was heated to 70° C. for an hour. The Acetic acid (2 ml) was added. Further the reaction mixture was stirred at 70° C. for 3 hours. Ethanol was distilled under vacuum to give a residue which was partitioned between Ethyl acetate (50 ml) and water (25 ml). Ethyl acetate was distilled under vacuum to give a crude product The crude product was solidified after stirring in Diethyl ether (10 ml). The solid was filtered under vacuum and dried to give a 700 mg of desired compound as a solid.

Workup

customreaction mixture
distillationEthanol was distilled under vacuum
customto give a residue which
customwas partitioned between Ethyl acetate (50 ml) and water (25 ml)
distillationEthyl acetate was distilled under vacuum
customto give a crude product The crude product
filtrationThe solid was filtered under vacuum
customdried

Sources & evidence

ORD record: ord-65166847c18840608ccd6904f3272fc5
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08378118B2

Reaction notes

Loading…