Sodium Hydroxide → HCID 13134787, compound
Reaction equation
[C:1]([CH2:3][C:4]1[CH:20]=[CH:19][C:7]([O:8][C:9]2[C:14]([CH2:15][C:16]([OH:18])=O)=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:6][CH:5]=1)#[N:2].[OH-:21].[Na+]>>[O:18]=[C:16]1[CH2:15][C:14]2[CH:13]=[CH:12][CH:11]=[N:10][C:9]=2[O:8][C:7]2[CH:19]=[CH:20][C:4]([CH2:3][C:1]([NH2:2])=[O:21])=[CH:5][C:6]1=2Participants
Procedure
To 1 g of 2-(4-cyanomethylphenoxy)-3-pyridylacetic acid was added 20 g of polyphosphoric acid, and the mixture was stirred in an oil bath at 151°-152° C. for 2.5 hours. After cooling, to this ice water was added to decompose excess polyphosphoric acid, and the mixture was basified with a 10% sodium hydroxide solution and extracted with ethyl acetate. The extract was washed with water and then a saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was removed by distillation to obtain a solid, which was chromatographed over 20 g of silica gel and eluted with n-hexane/acetone (2/1-1/1) to obtain crystals. These were recrystallized from acetone to give 300 mg (yield: 30%) of (5,6-dihydro-6-oxo benzo[b]pyrido-[3,2-f]oxepin-8-yl)-acetamide as white needle crystals having a melting point of 214°-217° C.
Workup
- additionwas added
- extractionextracted with ethyl acetate
- washThe extract was washed with water
- dry with materiala saturated sodium chloride solution and dried over anhydrous sodium sulfate
- customThe solvent was removed by distillation
- customto obtain a solid, which
- customwas chromatographed over 20 g of silica gel
- washeluted with n-hexane/acetone (2/1-1/1)
- customto obtain crystals
- customThese were recrystallized from acetone
Sources & evidence
- ORD record
- ord-4b91a74110924b24956dceb43ebb63ca
- Source dataset
- uspto-grants-1981_04
- Patent number
- US04263437
Reaction notes
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