2-Methoxybenzylamine → HCID 68577007, compound

HRID 1949062Notes

Reaction equation

C(O[C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11](Cl)[CH:10]=[CH:9]2)=[O:5])C.[CH3:17][O:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21][NH2:22]>>[CH3:17][O:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21][NH:22][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[C:11]([NH:22][CH2:21][C:20]1[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=1[O:18][CH3:17])[CH:10]=[CH:9]2)=[O:5]

Participants

Reactant 2

HCID 812922-Methoxybenzylamine

HCID 17834353Ethyl 2-chloroquinoline-6-carboxylate

Product 1

HCID 68577007HCID 68577007, compoundYield 9.4%

Conditions

Temperature: 120 °C

Procedure

A stirred mixture of 2-chloro-quinoline-6-carboxylic acid ethyl ester [CAS-No. 29969-56-0] (236 mg, 1.0 mmol) and commercially available 2-methoxy-benzylamine (412 mg, 3.0 mmol) was heated in a sealed tube for 16 h at 120° C. Purification by flash chromatography on silica gel (ethyl acetate/heptane) and crystallization of each of the two fractions (dichloromethane/hexane) yielded the title compound as a white solid (40 mg, 9%), MS (ISP) 428.3 [(M+H)+]; m.p. 217° C. as well as 2-(2-methoxy-benzylamino)-quinoline-6-carboxylic acid ethyl ester as a white solid (196 mg, 58%), MS (ISP) 337.3 [(M+H)+]; m.p. 108° C.

Workup

customPurification by flash chromatography
customon silica gel (ethyl acetate/heptane) and crystallization of each of the two fractions (dichloromethane/hexane)

Sources & evidence

ORD record: ord-51079c4b7a6142c08aec73c60c7e1b33
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399674B2

Reaction notes

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