2-(Dimethylamino)ethanol → 2-Dimethylamino-ethyl 2-(8-chloro-4-quinolinylamino)-5-fluoro-benzoate

HRID 224596Notes

Reaction equation

HRID 224596 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[NH:12][C:13]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16].[CH3:24][N:25]([CH3:29])[CH2:26]CO>>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[NH:12][C:13]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:14]=1[C:15]([O:17][CH2:18][CH2:24][N:25]([CH3:29])[CH3:26])=[O:16]

Participants

3

Reactant 2

HCID 79022-(Dimethylamino)ethanolHCID 23331697Methyl 2-(8-chloro-4-quinolinylamino)-5-fluoro-benzoate

Product 1

HCID 233316912-Dimethylamino-ethyl 2-(8-chloro-4-quinolinylamino)-5-fluoro-benzoate

Procedure

Using the procedure of Step B of Example 7, 6.61 g of the product of Step A and 4 ml of anhydrous 2-dimethylamino-ethanol were reacted to obtain 6.8 g of 2-dimethylamino-ethyl 2-(8-chloro-4-quinolinylamino)-5-fluoro-benzoate melting at 121°-122° C. 5.245 g of the said product were dissolved in 10 ml of anhydrous ethanol and 2.05 ml of an ethanol solution of 6.6 N hydrochloric acid were added thereto. The mixture was ice cooled and was vacuum filtered and the recovered product was washed with a 1-4 ethanol-ether mixture to obtain 5.34 g of the desired hydrochloride melting at 198° C.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-0907e9e1adff440684153e4ccdae9826
Source dataset
uspto-grants-1980_11
Patent number
US04233305

Reaction notes

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