5-Amino-2-methylphenol → 4-(3-Hydroxy-4-methylphenylamino)benzo[4,5]furo[3,2-b]pyridine-3-carbonitrile
Reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]2[C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[O:12][C:3]=12.[NH2:17][C:18]1[CH:23]=[C:22]([OH:24])[C:21]([CH3:25])=[CH:20][CH:19]=1>C(OCCO)C>[OH:24][C:22]1[CH:23]=[C:18]([NH:17][C:2]2[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]3[C:10]4[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=4[O:12][C:3]=23)[CH:19]=[CH:20][C:21]=1[CH3:25]Participants
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 200 mg (0.88 mmol) of 4-chlorobenzo[4,5]furo[3,2-b]pyridine-3-carbonitrile and 120 mg (0.97 mmol) of 5-amino-o-cresol in 6 mL of 2-ethoxyethanol is heated at 80° C. for 15 hours and then at reflux temperature for 10 hours. The reaction mixture is cooled to room temperature and partitioned between ethyl acetate and saturated sodium bicarbonate. The organic layer is washed with saturated sodium bicarbonate, dried over sodium sulfate and filtered through a pad of diatomaceous earth. Concentration in vacuo yields 200 mg (72%) of a beige solid, mp 240° C. dec. 1HNMR (DMSO-d6): δ 2.13 (s, 3H), 6.61 (dd, 1H), 6.68 (d, 1H), 7.03 (d, 1H), 7.51 (t, 1H), 7.63–7.74 (m, 2H), 8.15 (d, 1H), 8.62 (s, 1H), 9.40 (s, 1H), 9.66 (s, 1H). MS (ES, positive ion mode): m/z calcd for C19H13N3O2: 315.3, found: 315.9 (M+H)+. Analysis for C19H13N3O2.0.2H2O Calcd: C:71.54; H:4.22; N:13.17 Found: C:71.39; H:4.31; N: 12.99.
Workup
- temperatureat reflux temperature for 10 hours
- temperatureThe reaction mixture is cooled to room temperature
- custompartitioned between ethyl acetate and saturated sodium bicarbonate
- washThe organic layer is washed with saturated sodium bicarbonate
- dry with materialdried over sodium sulfate
- filtrationfiltered through a pad of diatomaceous earth
- concentrationConcentration in vacuo
Sources & evidence
- ORD record
- ord-8ef91b2ef0a14ddfbbe992fa0107ef7d
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07105531B2
Reaction notes
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