tert-Butanol → HCID 57017778, compound
Reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([OH:13])=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[C:26](O)([CH3:29])([CH3:28])[CH3:27].N12CCCN=C1CCCCC2>CN(C=O)C>[C:26]([O:12][C:11]([C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:1]=[CH:2][CH:3]=[CH:4]2)=[O:13])([CH3:29])([CH3:28])[CH3:27]Participants
Conditions
- Temperature
- 40 °C
Procedure
To a suspension of 6-quinolinecarboxylic acid (12 g, 69 mmol) in DMF (100 mL) was added 1,1′-Carbonyldiimidazole (11.2 g, 69.3 mmol) and the mixture stirred at 40° C. for 1 hour. tert-Butanol (13 mL, 139 mmol) and 1,8-Diazabicyclo[5.4.0]undec-7-ene (10.4 mL, 69.3 mmol) were added and the mixture was stirred at 80° C. for 4 h. After cooling to room temperature the reaction mixture was quenched with water (400 mL) and extracted with ethyl acetate/heptane (1:3, 2×400 mL). The organic layer was dried over MgSO4 and concentrated to give quinoline-6-carboxylic acid t-butyl ester (14.54 g, 92%). 1H NMR (400 MHz, CDCl3) δ 1.63 (9H, s), 7.42-7.46 (1H, m), 8.10 (1H, d), 8.23 (1H, d), 8.26 (1H, d), 8.50 (1H, d), 8.96-8.98 (1H, m). LCMS: Retention time: 1.42 min. MS (ESI) m/z 230 (M+H)+
Workup
- stirringthe mixture was stirred at 80° C. for 4 h
- temperatureAfter cooling to room temperature the reaction mixture
- customwas quenched with water (400 mL)
- extractionextracted with ethyl acetate/heptane (1:3, 2×400 mL)
- dry with materialThe organic layer was dried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-ca6d3c3f6c27450f838ffc92819adb9d
- Source dataset
- uspto-grants-2011_06
- Patent number
- US07964732B2
Reaction notes
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