Sodium Hydroxide → HCID 89783435, compound

HRID 1055920Notes

Reaction equation

HRID 1055920 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[C:9]([C:11]3[CH:12]=[CH:13][CH:14]=[C:15]4[C:20]=3[N:19]=[C:18]([C:21]([O:23]C)=[O:22])[CH:17]=[CH:16]4)[NH:10][C:6]=2[CH2:5][CH2:4][NH:3]1.[OH-].[Na+]>C1COCC1>[O:1]=[C:2]1[C:7]2[CH:8]=[C:9]([C:11]3[CH:12]=[CH:13][CH:14]=[C:15]4[C:20]=3[N:19]=[C:18]([C:21]([OH:23])=[O:22])[CH:17]=[CH:16]4)[NH:10][C:6]=2[CH2:5][CH2:4][NH:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 89783876HCID 89783876, compound

Product 1

HCID 89783435HCID 89783435, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 8-(4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl)quinoline-2-carboxylate (0.84 g, 2.62 mmol) was dissolved in THF (25 mL), NaOH 1.00 N (2.62 mL, 2.62 mmol) was added, and the resulting solution was stirred at RT for 3 h, then at 40° C. for 2 h. The reaction mixture was then concentrated in vacuo the pH was adjusted to <4 using 5 N HCl. A precipitate formed and was isolated by filtration to give 8-(4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-2-yl)quinoline-2-carboxylic acid (647 mg, 2.11 mmol, 80% yield) as a dark-brown solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 13.71 (br. s., 1H), 12.72 (br. s., 1H), 8.59 (d, J=8.4 Hz, 1H), 8.26 (d, J=7.4 Hz, 1H), 8.16 (d, J=8.6 Hz, 1H), 7.89 (d, J=8.0 Hz, 1H), 7.72 (t, J=7.7 Hz, 1H), 7.30-7.34 (m, 1H), 7.04 (br. s., 1H), 3.46 (t, J=6.5 Hz, 2H), 2.90 (t, J=6.7 Hz, 2H). m/z (ESI, +ve ion) 308.0 (M+H)+.

Workup

  1. waitat 40° C. for 2 h
  2. concentrationThe reaction mixture was then concentrated in vacuo the pH
  3. customA precipitate formed
  4. customwas isolated by filtration

Sources & evidence

ORD record
ord-932fc056fdc447a99c1cb86db48c6473
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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