Hydrochloric Acid → HCID 67440913, compound

HRID 1800878Notes

Reaction equation

HRID 1800878 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([Cl:24])[CH:8]=[C:9]2[C:14]=1[NH:13][CH:12]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[CH:16]=1)[C:11]([CH3:23])([CH3:22])[CH2:10]2)=[O:4].Cl>CO.O1CCCC1.[OH-].[Na+].O>[NH2:21][C:17]1[CH:16]=[C:15]([CH:12]2[C:11]([CH3:23])([CH3:22])[CH2:10][C:9]3[C:14](=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=[C:7]([Cl:24])[CH:8]=3)[NH:13]2)[CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 2

HCID 313Hydrochloric AcidHCID 67441304HCID 67441304, compound

Product 1

HCID 67440913HCID 67440913, compoundYield 98.6%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-(3-amino-phenyl)-6-chloro-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid methyl ester (0.8 g, 2.3 mmol) in methanol (50 mL) and tetrahydrofuran (100 mL), 30% sodium hydroxide in water (20 mL) was stirred at 60° C. for 12 h. The mixture was neutralized with a 3 N aqueous hydrochloric acid solution and extracted with ethyl acetate (2×100 mL), washed with water, dried over anhydrous sodium sulfate and then concentrated in vacuo to afford 2-(3-amino-phenyl)-6-chloro-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid (0.75 g, 65%) as a brown solid which was used for next step without further purification: LC/MS m/e calcd for C18H19ClN2O2 (M+H)+: 331.82, observed: 331.1.

Workup

  1. extractionextracted with ethyl acetate (2×100 mL)
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-88d781b4158f4037b5c2ff67c1258839
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

Loading…