Toluene → 2-Dimethylaminoethyl 2-(7-chloro-4-quinolinylamino)-5-fluorobenzoate

HRID 224588Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C:13]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:14]=3[C:15]([O:17][CH3:18])=[O:16])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[CH3:24][N:25]([CH2:27]CO)[CH3:26].C1(C)C=CC=CC=1.[H-].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C:13]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:14]=3[C:15]([O:17][CH2:18][CH2:24][N:25]([CH3:27])[CH3:26])=[O:16])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 4 g of the ester of Example 1, 2.45 ml of dimethylaminoethanol and 50 ml of anhydrous toluene was heated to reflux and then cooled to 50° C. and 95 mg of a 50% sodium hydride oil suspension was added thereto. The mixture was again heated to reflux and was then cooled to 40° C. and 0.2 ml of acetic acid were added thereto. The mixture was evaporated to dryness and the residue was dissolved in methylene chloride. The solution was filtered and the filtrate was washed with water, dried and filtered. The filtrate was evaporated to dryness to obtain 4.01 g of 2-dimethylaminoethyl 2-(7-chloro-4-quinolinylamino)-5-fluorobenzoate.

Workup

temperaturewas heated
temperatureto reflux
temperatureThe mixture was again heated
temperatureto reflux
temperaturewas then cooled to 40° C.
customThe mixture was evaporated to dryness
dissolutionthe residue was dissolved in methylene chloride
filtrationThe solution was filtered
washthe filtrate was washed with water
customdried
filtrationfiltered
customThe filtrate was evaporated to dryness

Sources & evidence

ORD record: ord-a64622601a574964a44d47d361a9de22
Source dataset: uspto-grants-1980_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04233305

Reaction notes

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