Acetic Acid → HCID 69205369, compound
Reaction equation
COC([C:5]1[C:6]([C:17]2[CH:25]=[CH:24][C:20]3[O:21][CH2:22][O:23][C:19]=3[CH:18]=2)(C#N)[C:7]2[C:12]([C:13]=1N)=[CH:11][CH:10]=[CH:9][CH:8]=2)=O.S(=O)(=O)(O)[OH:27].[C:31]([OH:34])(=[O:33])C>>[O:21]1[C:20]2[CH:24]=[CH:25][C:17]([C:6]3([C:31]([OH:34])=[O:33])[C:7]4[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:13](=[O:27])[CH2:5]3)=[CH:18][C:19]=2[O:23][CH2:22]1Participants
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 3-amino-1-benzo[1,3]dioxol-5-yl-1-cyano-1H-indene-2-carboxylic acid methyl ester (10 g) and acetic acid, (30 mL) were heated to 100° C.; 60% aqueous sulfuric acid (20 mL) was added with stirring during 30 min. The mixture was heated to 110° C. for 6 h, cooled to rt, extracted with toluene (50+10 mL), washed with water (3×100 mL), extracted with 0.1 M aqueous sodium hydroxide (100+20 mL), acidified with concentrated hydrochloric acid, extracted with toluene (25+10 mL), and filtrated through activated carbon. Removal of the toluene gave 80% of 1-(benzo[1,3]dioxol-5-yl)-3-oxo-indan-1-carboxylic acid. The acid was subsequently decarboxylated by heating to 100° C. in N-methylpyrrolidone (15 mL) for 1 h. After cooling, the solution was poured into water (40 mL) with efficient stirring. Filtration, washing with water (5×20 mL), dissolution in ethyl acetate (40 mL), filtration through activated carbon and removal of the ethyl acetate gave 80% of 3-(benzo[1,3]dioxol-5-yl)-indan-1-one.
Workup
- temperatureThe mixture was heated to 110° C. for 6 h
- temperaturecooled to rt
- extractionextracted with toluene (50+10 mL)
- washwashed with water (3×100 mL)
- extractionextracted with 0.1 M aqueous sodium hydroxide (100+20 mL)
- extractionextracted with toluene (25+10 mL)
- filtrationfiltrated through activated carbon
- customRemoval of the toluene
Sources & evidence
- ORD record
- ord-4bf77be52fab4c619845db5a668e0dc7
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07351734B2
Reaction notes
Loading…