Tert-Butyl nitrite → 2-Chloro-6,7-dihydro-5H-quinazolin-8-one oxime
Reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1.CC([O-])(C)C.[K+].[N:18](OC(C)(C)C)=[O:19]>C1COCC1>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][C:5](=[N:18][OH:19])[C:4]=2[N:3]=1Participants
5
Conditions
- Temperature
- -78 °C
Procedure
2-Chloro-5,6,7,8-tetrahydro-quinazoline (Eur. J. Med. Chem. 1982, 17, 75)(1.0 g; 5.9 mmol) is dissolved in THF (80 ml) and cooled to −78° C. KOtBu (667 mg; 5.9 mmol) in THF (10 ml) is added dropwise and stirred for 5 minutes after complete addition. t-Butyl nitrite (2 ml; 27.8 mmol) is added to the orange solution and the reaction mixture warmed to room temperature. After 10 minutes the reaction mixture is poured on water/HOAc (800/1 ml) and extracted with ethyl acetate three times. The combined organic phases are dried over Na2SO4, filtered and evaporated to dryness to deliver the title compound as yellow-orange crystals (1.1 g; 95%).
Workup
- additionafter complete addition
- temperaturethe reaction mixture warmed to room temperature
- additionAfter 10 minutes the reaction mixture is poured on water/HOAc (800/1 ml)
- extractionextracted with ethyl acetate three times
- dry with materialThe combined organic phases are dried over Na2SO4
- filtrationfiltered
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-913843b274264615a62cb2bb44c4e11f
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07838674B2
Reaction notes
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