Hydrochloric Acid → HCID 178424290, compound

HRID 2352979Notes

Reaction equation

[CH3:1][C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([C:15]2[CH:23]=[C:22]3[C:18]([CH2:19][C:20](=[O:24])[NH:21]3)=[CH:17][CH:16]=2)=[O:14])[CH:8]=1)=[O:5].[CH:29](OCC)=[O:30].[O-]CC.[Na+].Cl>C(O)C>[OH:30][CH:29]=[C:19]1[C:18]2[C:22](=[CH:23][C:15]([C:13]([C:9]3[CH:8]=[C:7]([NH:6][C:4](=[O:5])[C:3]4[CH:25]=[CH:26][CH:27]=[CH:28][C:2]=4[CH3:1])[CH:12]=[CH:11][CH:10]=3)=[O:14])=[CH:16][CH:17]=2)[NH:21][C:20]1=[O:24]

Participants

Conditions

Temperature: 78 °C

Procedure

2-Methyl-N-[3-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-benzamide (5.00 g, 13.499 mmol) and ethyl formate (3.24 mL, 40.3 mmol) were dissolved in anhydrous ethanol (135 mL). The resulting solution was treated in dropwise fashion with a 21 wt % solution of sodium ethoxide in ethanol (25.2 mL, 67.47 mmol). This reaction mixture was heated at 78° C. for 0.5 h, producing a black oil. Subsequently, the reaction mixture was cooled to room temperature, and then the reaction pH was adjusted to pH 1 with dropwise addition of 1M HCl(aq) causing the formation of a light yellow precipitate. The suspension was filtered and the solids were washed with 0° C. EtOH to afford the pure N-[3-(3-Hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-2-methyl-benzamide (4.464 g, 11.2 mmol, 81%).

Workup

customproducing a black oil
temperatureSubsequently, the reaction mixture was cooled to room temperature
filtrationThe suspension was filtered
washthe solids were washed with 0° C

Sources & evidence

ORD record: ord-ec155135daee4a3f8c317c761209931a
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07749530B2

Reaction notes

Loading…