Hydrochloric Acid → HCID 21892168, compound

HRID 720432Notes

Reaction equation

HRID 720432 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][CH:27]=1)[C:6]([C:8]1[N:12]2[C:13]3[C:18]([CH:19]=[CH:20][C:11]2=[C:10]([C:21]([O:23]C)=[O:22])[CH:9]=1)=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:7].Cl>CO.[OH-].[Na+]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][CH:27]=1)[C:6]([C:8]1[N:12]2[C:13]3[C:18]([CH:19]=[CH:20][C:11]2=[C:10]([C:21]([OH:23])=[O:22])[CH:9]=1)=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:7]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86596026HCID 86596026, compound

Product 1

HCID 21892168HCID 21892168, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 1-(3-methoxy-benzoyl)-pyrrolo[1,2-a]quinoline-3-carboxylic acid, methyl ester (130 mg, 0.348 mmol) in MeOH (5 mL) and NaOH (2N, 5 mL) was stirred at 50° C. for 24 h. The reaction mixture was acidified to pH=3 with 10% HCl to produce a light yellow precipitate. The mixture was filtered and the solid was washed with water, and dried in vacuo (114 mg, 95%): 1H NMR (DMSO-D6): 8.28 (d, J=9.3 Hz, 1H), 8.04 (dd, J=1.2, 8.7 Hz, 1H), 7.97 (d, J=9.3 Hz, 2H), 7.70–7.52 (m, 5H), 7.46 (s, 1H), 7.33 (m, 1H), 3.86 (s, 3H), 3.35 (s, 1H).

Workup

  1. customto produce a light yellow precipitate
  2. filtrationThe mixture was filtered
  3. washthe solid was washed with water
  4. customdried in vacuo (114 mg, 95%)

Sources & evidence

ORD record
ord-f9e14f1fe7a249038a97352767c3034b
Source dataset
uspto-grants-2006_11
Patent number
US07135480B2

Reaction notes

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