Hydrochloric Acid → 4-(2-Methyl-quinolin-4-ylmethoxy)-phenylamine hydrochloride

HRID 535044Notes

Reaction equation

HRID 535044 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=[C:18]([CH3:26])[CH:17]=2)=[CH:10][CH:9]=1)(C)(C)C.[ClH:28].C(OCC)C>C(OCC)(=O)C.O1CCOCC1>[ClH:28].[CH3:26][C:18]1[CH:17]=[C:16]([CH2:15][O:14][C:11]2[CH:10]=[CH:9][C:8]([NH2:7])=[CH:13][CH:12]=2)[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 57562794[4-(2-Methylquinolin-4-ylmethoxy)phenyl]carbamic acid tert-butyl ester

Product 1

HCID 673042194-(2-Methyl-quinolin-4-ylmethoxy)-phenylamine hydrochloride

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of [4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-carbamic acid tert-butyl ester (1.5 g, 4.1 mmol) in ethyl acetate (5 mL) was added 4 N HCl in dioxane (20 mL) and the mixture was stirred at room temperature for 3 h. Ethyl ether was then added and the precipitate was filtered and washed with ethyl ether to provide 1.3 g of the desired free amine as an HCl salt, which was used in the following reaction without further purification. MS (ESI): 265.0 (M+H+).

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed with ethyl ether

Sources & evidence

ORD record
ord-e2dec06371ee43758afcbbdd13562850
Source dataset
uspto-grants-2014_10
Patent number
US08853243B2

Reaction notes

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