Acetic Acid → HCID 65098528, compound
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:8][C:9]1[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([F:18])[C:10]=1[CH:11]=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClC(Cl)C.C(Cl)Cl.O>[F:8][C:9]1[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([F:18])[C:10]=1[CH2:11][NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
9
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 70 °C
Procedure
A mixture of aniline (3.80 mL, 41.7 mmol), 2,4,6-trifluorobenzaldehyde (7.35 g, 45.9 mmol) and glacial acetic acid (6.0 mL, 104.4 mmol) in dichloroethane (100 mL) was heated at 70° C. for 2.5 h. After cooling to rt, sodium triacetoxyborohydride (17.7 g, 83.5 mmol) was added and the mixture stirred at rt for 1.5 h, before the cautious addition of H2O (100 mL), followed by 10M aqueous NaOH (30 mL) and DCM (50 mL). The phases were separated, and the aqueous phase was extracted with DCM (2×100 mL), the combined organic phases were washed with brine (50 mL) and concentrated in vacuo. Purification by gradient column chromatography eluting with 0-6% EtOAc in iso-hexane yielded the title compound (9.90 g, 41.7 mmol).
Workup
- temperatureAfter cooling to rt
- customThe phases were separated
- extractionthe aqueous phase was extracted with DCM (2×100 mL)
- washthe combined organic phases were washed with brine (50 mL)
- concentrationconcentrated in vacuo
- customPurification by gradient column chromatography
- washeluting with 0-6% EtOAc in iso-hexane
Sources & evidence
- ORD record
- ord-b1b17dabc81c4f4aabdeb969c17fda9a
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09249160B2
Reaction notes
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