Sodium Hydroxide → HCID 67442030, compound

HRID 1801313Notes

Reaction equation

HRID 1801313 reaction equation
[CH:1]1([C:5]([NH:7][C:8]2[CH:9]=[C:10]([CH:15]3[C:24]([CH3:26])([CH3:25])[CH2:23][C:22]4[C:17](=[CH:18][CH:19]=[C:20]([C:27]([O:29]C)=[O:28])[CH:21]=4)[NH:16]3)[CH:11]=[CH:12][C:13]=2[F:14])=[O:6])[CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([C:5]([NH:7][C:8]2[CH:9]=[C:10]([CH:15]3[C:24]([CH3:26])([CH3:25])[CH2:23][C:22]4[C:17](=[CH:18][CH:19]=[C:20]([C:27]([OH:29])=[O:28])[CH:21]=4)[NH:16]3)[CH:11]=[CH:12][C:13]=2[F:14])=[O:6])[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67442169HCID 67442169, compound

Product 1

HCID 67442030HCID 67442030, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 2-(3-(cyclobutanecarboxamido)-4-fluorophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (0.26 mmol, 1.0 eq.) and 4.5 mL sodium hydroxide (1 mol/L) in 3 mL methanol was stirred at reflux for 1-2 h. LC-MS indicated that the starting material was consumed completely. The methanol was removed by reduced pressure. The residue was acidified pH to 5-6 with 1 M hydrochloric acid. A lot of precipitates were formed and collected by filtration to afford 2-(3-(cyclobutanecarboxamido)-4-fluorophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a white solid; Yield: 80%; MS (ESI+APCI) M+1=397.

Workup

  1. temperatureat reflux for 1-2 h
  2. customwas consumed completely
  3. customThe methanol was removed by reduced pressure
  4. customA lot of precipitates
  5. customwere formed
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-5f4b9f576ff34ce1addd52074a573584
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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