Sodium Hydroxide → HCID 70495643, compound

HRID 2407974Notes

Reaction equation

C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[CH:16]=1)[CH2:9][C:8]12[CH2:30][CH2:29][CH2:28][CH2:27]1)=[O:4].[OH-].[Na+]>O1CCCC1.CO.O>[O:24]1[CH2:25][CH2:26][N:21]([C:17]2[CH:16]=[C:15]([CH:10]3[CH2:9][C:8]4([CH2:30][CH2:29][CH2:28][CH2:27]4)[C:7]4[C:12](=[CH:13][CH:14]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=4)[NH:11]3)[CH:20]=[CH:19][CH:18]=2)[CH2:22][CH2:23]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of 2′-(3-morpholinophenyl)-2′,3′-dihydro-1′H-spiro[cyclopentane-1,4′-quinoline]-6′-carboxylic acid methyl ester (406.0 mg, 1.0 mmol) in tetrahydrofuran (10.0 mL) and methanol (10.0 mL) was added 3 N sodium hydroxide (2.0 mL). The reaction mixture was stirred at 80° C. for 6 h, and then diluted with water (10.0 mL), extracted with diethyl ether (20.0 mL). The organic layer was discarded. The aqueous layer was acidified with concentrated hydrochloric acid to pH 4 and extracted with ethyl acetate (40 mL×3). The combined organic layers were dried over anhydrous sodium sulfate. The solvent was removed in vacuo and afforded 2′-(3-morpholinophenyl)-2′,3′-dihydro-1′H-spiro[cyclopentane-1,4′-quinoline]-6′-carboxylic acid (352.8 mg, 90%) as a light yellow powder: MS (ESI) M+1=393.1.

Workup

extractionextracted with diethyl ether (20.0 mL)
extractionextracted with ethyl acetate (40 mL×3)
dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-5fd0601fc2d949cd87d89b73a8b8338f
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809369B2

Reaction notes

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