Carbon Dioxide → HCID 11324953, compound
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N:9]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]1=2.[Li]CCCC.[C:28](=[O:30])=[O:29]>C1COCC1>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:16]([C:28]([OH:30])=[O:29])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:22]1=2Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 4.28 g of N-(2,6-dimethylphenyl)acridan (15 mmol) in 100 mL of THF under argon was cooled to −78° C. After 10 min, 7.6 mL of n-BuLi (18.7 mmol) was added. The black solution stirred 30 min and then the temperature was raised to 0° C. for 40 min. The reaction was again cooled to −78° C. and 270 g of crushed dry ice was added to the reaction mixture to form a yellow solution with a white precipitate that dissolved once the reaction was warmed to room temperature. The reaction was stirred for 16 h at room temperature, and then concentrated and taken up in a mixture of water and diethyl ether. The aqueous portion was acidified with HCl to afford a white precipitate, which was filtered and dried to give 4.8 g of N-(2,6-dimethylphenyl)acridan-9-carboxylic acid as a white solid (97%).
Workup
- temperatureThe reaction was again cooled to −78° C.
- customto form a yellow solution with a white precipitate
- dissolutionthat dissolved once the reaction
- temperaturewas warmed to room temperature
- stirringThe reaction was stirred for 16 h at room temperature
- concentrationconcentrated
- additiontaken up in a mixture of water and diethyl ether
- customto afford a white precipitate, which
- filtrationwas filtered
- customdried
Sources & evidence
- ORD record
- ord-91dbef275f294b8687aaf0e99dfd0154
- Source dataset
- uspto-grants-2002_06
- Patent number
- US06410732B2
Reaction notes
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