Sodium Hydroxide → 2-(3-(Cyclopropanecarboxamido)-4-fluorophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid

HRID 2045583Notes

Reaction equation

HRID 2045583 reaction equation
[CH:1]1([C:4]([NH:6][C:7]2[CH:8]=[C:9]([CH:14]3[C:23]([CH3:25])([CH3:24])[CH2:22][C:21]4[C:16](=[CH:17][CH:18]=[C:19]([C:26]([O:28]C)=[O:27])[CH:20]=4)[NH:15]3)[CH:10]=[CH:11][C:12]=2[F:13])=[O:5])[CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([C:4]([NH:6][C:7]2[CH:8]=[C:9]([CH:14]3[C:23]([CH3:25])([CH3:24])[CH2:22][C:21]4[C:16](=[CH:17][CH:18]=[C:19]([C:26]([OH:28])=[O:27])[CH:20]=4)[NH:15]3)[CH:10]=[CH:11][C:12]=2[F:13])=[O:5])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67443191Methyl 2-(3-(cyclopropanecarboxamido)-4-fluorophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate

Product 1

HCID 674406882-(3-(Cyclopropanecarboxamido)-4-fluorophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acidYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 2-(3-(cyclopropanecarboxamido)-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 71 mg of 2-(3-(cyclopropanecarboxamido)-4-fluorophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a white solid; yield: 72%. MS (ESI+APCI) M+1=383.

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-d3b1c5843c6c4bb68b3d15eeaac61008
Source dataset
uspto-grants-2013_11
Patent number
US08586747B2

Reaction notes

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