Pyridine → HCID 70108068, compound

HRID 1740772Notes

Reaction equation

[C:1]([C:9]1[CH:10]=[C:11](OC)[CH:12]=[C:13]2[C:17]=1[NH:16][CH2:15][CH2:14]2)(=[O:8])C1C=CC=CC=1.[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl.NCC(O[CH2:32][CH3:33])=O.[C:34](=[O:37])([O-])[O-].[Na+].[Na+].Cl[CH2:41]Cl>O>[CH3:34][O:37][C:15]1[N:16]2[C:24]([C:23]3[CH:33]=[CH:32][CH:41]=[CH:21][CH:22]=3)=[CH:25][NH:20][C:1](=[O:8])[C:9]3=[CH:10][CH2:11][CH2:12][C:13]([CH:14]=1)=[C:17]23

Participants

Conditions

Temperature: 112.5 °C

Procedure

4.71 g (18.6 mmol) of 7-benzoyl-5-methoxyindoline are introduced into 75 ml of pyridine, followed by 16.2 g (116 mmol) of ethyl glycinate hydrochloride. The mixture is heated to 110-115° C. with stirring while distilling off the light fractions which form. After 12 hours, the mixture is cooled and 100 ml of a 2.5% solution of sodium carbonate in water and 100 ml of dichloromethane are added. The aqueous phase is separated out and extracted with 100 ml of dichloromethane. The organic phases are combined and washed with water. The solvent is evaporated off and the residue is then purified by flash chromatography on a column of silica, the eluent used being a gradient of acetone in dichloromethane. 4.15 g of purified product in the form of a brown resin are obtained.

Workup

distillationwhile distilling off the light fractions which
customform
temperaturethe mixture is cooled
customThe aqueous phase is separated out
extractionextracted with 100 ml of dichloromethane
washwashed with water
customThe solvent is evaporated off
customthe residue is then purified by flash chromatography on a column of silica

Sources & evidence

ORD record: ord-d470e03fbdbc4695895c049fdcaa78f0
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05972927

Reaction notes

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