Water → 4-chloro-7-fluoro-1H-indole-2-carboxylic acid ethyl ester
Reaction equation
C(OC(=O)C(=N[NH:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[F:16])C)C.[C:18]1(C)C=CC(S(O)(=O)=O)=C[CH:19]=1.O.[C:30](=[O:33])(O)[O-:31].[Na+].[C:35]1(C)C=CC=C[CH:36]=1>>[CH2:35]([O:31][C:30]([C:18]1[NH:8][C:9]2[C:14]([CH:19]=1)=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=2[F:16])=[O:33])[CH3:36]Participants
6
Procedure
2-[(5-Chloro-2-fluoro-phenyl)-hydrazono]-propionic acid ethyl ester (13.2 g, 51 mmol) was dissolved in toluene, p-toluenesulfonic acid (10 g, 51 mmol) was added and the mixture was heated to reflux for 24 h with separation of water. The mixture was cooled, neutralized with saturated sodium bicarbonate (400 mL) and extracted thrice with ethyl acetate. Organic phases were pooled, washed with brine, dried with MgSO4 and the solvent was removed in vacuo. The residue was triturated with hexane to yield the title product as yellowish solid (2.9 g, 23%); EI-MS: m/e=241.1 (M+).
Workup
- temperaturethe mixture was heated
- temperatureThe mixture was cooled
- extractionextracted thrice with ethyl acetate
- washwashed with brine
- dry with materialdried with MgSO4
- customthe solvent was removed in vacuo
- customThe residue was triturated with hexane
Sources & evidence
- ORD record
- ord-5199bc7cef8d4b5599e0af3edca56b8d
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07253281B2
Reaction notes
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