Hydrochloric Acid → 3-amino-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-3,4-dihydroquinolin-2(1H)-one

HRID 2070129

Reaction equation

[O:1]=[C:2]1[CH:11]([NH:12]C(=O)OC(C)(C)C)[CH2:10][C:9]2[C:4](=[C:5]([N:20]3[CH2:24][CH2:23][CH2:22][C:21]3=[O:25])[CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:26][C:27]1[CH:31]=[CH:30][S:29][CH:28]=1.Cl.[OH-].[Na+]>C(O)C>[NH2:12][CH:11]1[CH2:10][C:9]2[C:4](=[C:5]([N:20]3[CH2:24][CH2:23][CH2:22][C:21]3=[O:25])[CH:6]=[CH:7][CH:8]=2)[N:3]([CH2:26][C:27]2[CH:31]=[CH:30][S:29][CH:28]=2)[C:2]1=[O:1]

Participants

Conditions

Temperature: 60 °C

Procedure

tert-Butyl 2-oxo-8-(2-oxopyrrolidin-1-yl)-1-(thiophen-3-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-ylcarbamate (399 g) was suspended in ethanol (2 L), and concentrated hydrochloric acid (555 mL) was added to the suspension, followed by stirring at 60° C. for 30 minutes. The reaction mixture was neutralized with 25% aqueous sodium hydroxide solution under cooling on ice. The resultant mixture was partitioned between chloroform and water, and the aqueous layer was extracted with chloroform. The organic layers were combined, and the combined organic layer was dried over sodium sulfate. The solvent was evaporated under reduced pressure, whereby the title compound (418 g) in a crude form was yielded, which was employed in the subsequent reaction step without performing further purification.

Workup

temperatureunder cooling on ice
customThe resultant mixture was partitioned between chloroform and water
extractionthe aqueous layer was extracted with chloroform
dry with materialthe combined organic layer was dried over sodium sulfate
customThe solvent was evaporated under reduced pressure, whereby the title compound (418 g) in a crude form
customwas yielded
customwhich was employed in the subsequent reaction step
custompurification

Sources & evidence

ORD record: ord-5d50a66e06604a60bfd1055d6f69ce1e
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299255B2

Linked notes

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