Hydrochloric Acid → 6-[5-(2-Amino-ethoxy)-pyridin-3-yl]-1-methyl-3,4-dihydro-1H-quinolin-2-one hydrochloride

HRID 1774807Notes

Reaction equation

HRID 1774807 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[N:13][CH:14]=[C:15]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[N:23]([CH3:27])[C:22](=[O:28])[CH2:21][CH2:20]3)[CH:16]=1)(C)(C)C.[ClH:30].O1CCOCC1>CO>[ClH:30].[NH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[C:15]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[N:23]([CH3:27])[C:22](=[O:28])[CH2:21][CH2:20]3)[CH:14]=[N:13][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 71533455{2-[5-(1-Methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-yloxy]-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 866791646-[5-(2-Amino-ethoxy)-pyridin-3-yl]-1-methyl-3,4-dihydro-1H-quinolin-2-one hydrochlorideYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of {2-[5-(1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-yloxy]-ethyl}-carbamic acid tert-butyl ester (example 39, 0.06 g, 0.151 mmol) in MeOH (1 mL) was added 4M HCl in dioxane (0.151 mL, 0.604 mmol) and the reaction mixture was stirred at room temperature over night. The resulting suspension was filtered off and the solid material was triturated in diethyl ether, filtered off and further dried in a high vacuum to give the title compound (0.046 g, 91%) as a white solid. MS: 298.3 (M+H+).

Workup

  1. filtrationThe resulting suspension was filtered off
  2. customthe solid material was triturated in diethyl ether
  3. filtrationfiltered off
  4. customfurther dried in a high vacuum

Sources & evidence

ORD record
ord-2cfd5ebe07b94896afc17e8226eccecf
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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