Sodium Carbonate → HCID 9884463, compound

HRID 1084727

Reaction equation

HRID 1084727 reaction equation
[Na].[NH2:2][C:3]1[C:7]([CH3:8])=[CH:6][S:5][C:4]=1C(O)=O.[CH3:12][O:13][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:23]=1[N:22]=[CH:21][C:20]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:19]2Cl.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.C(O)(=O)C>[CH3:12][O:13][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:23]=1[N:22]=[CH:21][C:20]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:19]2[NH:2][C:3]1[C:7]([CH3:8])=[CH:6][S:5][CH:4]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 3045573-Quinolinecarboxylic acid, 4-chloro-8-methoxy-, ethyl esterHCID 5360545SodiumHCID 149896783-Amino-4-methylthiophene-2-carboxylic acid

Product 1

HCID 9884463HCID 9884463, compoundYield 31.4%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

The sodium salt of 3-amino-4-methylthiophene-2-carboxylic acid (7.2 g, 0.04 mol) and ethyl 8-methoxy-4-chloroquinoline-3-carboxylate (5.39 g, 0.02 mol) in toluene (75 ml), ethanol (55 ml) and glacial acetic acid (10 ml) were stirred at room temperature for five days. The solvents were removed by evaporation at reduced pressure to give a dark-green slurry. 10% aqueous sodium carbonate was added and the insoluble solid filtered off, washed well with water and dried. This material was crystallised from ethyl acetate (with charcoaling) to give the title compound as pale yellow crystals (2.15 g), m.p. 162°-164°.

Workup

  1. customThe solvents were removed by evaporation at reduced pressure
  2. customto give a dark-green slurry
  3. filtrationthe insoluble solid filtered off
  4. washwashed well with water
  5. customdried
  6. customThis material was crystallised from ethyl acetate (with charcoaling)

Sources & evidence

ORD record
ord-87d67d2a1bf3431799652c6e30b4cd43
Source dataset
uspto-grants-1991_04
Patent number
US05006535

Linked notes

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