Hydrochloric Acid → 2-Tetrahydropyranylmethyl 2-(7-chloro-4-quinolyl)aminobenzoate

HRID 35548

Reaction equation

HRID 35548 reaction equation
FC(F)(F)[C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH:13][C:14]3[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=3[C:16]([O:18][CH3:19])=[O:17])=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.OC[CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][O:29]1.[Na].[ClH:35]>C(OC(C)C)(C)C.C1(C)C=CC=CC=1>[Cl:35][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH:13][C:14]3[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=3[C:16]([O:18][CH2:19][CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][O:29]3)=[O:17])=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7524Tetrahydropyran-2-methanolHCID 5360545SodiumHCID 21294482Methyl 2-(7-trifluoromethyl-4-quinolyl)aminobenzoate

Product 1

HCID 212944742-Tetrahydropyranylmethyl 2-(7-chloro-4-quinolyl)aminobenzoateYield 67%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 7914Diisopropyl EtherSolvent

Procedure

By treating 15.4 g of methyl 2-(7-chloro-4-quinolyl)aminobenzoate (II, R=Cl, R"=CH3), 8.46 g of 2-hydroxymethyltetrahydropyran, 125 ml of toluene and in the presence of sodium, as described in Example 1, 19.8 g of a crude material are isolated. This material is dissolved in 250 ml of diisopropyl ether and 7 ml of hydrochloric acid (g) 10N ethanolic solution are added under cooling in water-ice bath. After 15 minutes the precipitated hydrochloride is filtered off, dried (19.45 g; 91%) and recrystallized in acetonitrile. 14.34 g (yield: 67%) of the hydrochloride--yellow solid--are obtained with m.p. 187°-187.5° C. and elemental analysis C, H, N, Cl correct.

Workup

  1. customare isolated
  2. filtrationAfter 15 minutes the precipitated hydrochloride is filtered off
  3. customdried (19.45 g; 91%)
  4. customrecrystallized in acetonitrile

Sources & evidence

ORD record
ord-358f88f48e804101b8422a64e4e175f2
Source dataset
uspto-grants-1988_08
Patent number
US04767767

Linked notes

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