Hydrochloric Acid → HCID 178517286, compound

HRID 641055Notes

Reaction equation

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

Participants

Conditions

Temperature: 78 °C

Procedure

6-[3-(benzylamino)benzoyl]-1,3-dihydro-2H-indol-2-one (0.057 g, 0.167 mmol) and ethyl formate (0.040 mL, 0.500 mmol) were dissolved in anhydrous ethanol (1.67 mL). The resulting solution was treated in dropwise fashion with a 21 wt % solution of sodium ethoxide in ethanol (0.310 mL, 0.833 mmol). This reaction mixture was heated at 78° C. for 1 h, producing a black oil. 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 tan precipitate. The suspension was filtered yielding 6-(3-Benzylamino-benzoyl)-3-[1-hydroxy-meth-(Z)-ylidene]-1,3-dihydro-indol-2-one as an orange solid (0.021 g, 0.056 mmol, 34%) which was carried on without further purification.

Workup

customproducing a black oil
temperatureThe reaction mixture was cooled to room temperature
filtrationThe suspension was filtered

Sources & evidence

ORD record: ord-6d7109379e3e4140945583f6daa734da
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07692005B2

Reaction notes

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