Ethanol → Pirolate

HRID 442201Notes

Reaction equation

HRID 442201 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([NH2:15])[C:7]([C:16]([O:18]CC)=O)=[CH:6]2.Cl.[C:22]([C:27](=[NH:31])OCC)([O:24][CH2:25][CH3:26])=[O:23].C(N(CC)CC)C.C(O)C>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]1[N:15]=[C:27]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[NH:31][C:16](=[O:18])[C:7]1=[CH:6]2

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 12773119Ethyl 2-ethoxy-2-iminoacetate hydrochlorideHCID 54052734Ethyl 2-amino-6,7-dimethoxyquinoline-3-carboxylate

Product 1

HCID 135445830Pirolate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

An alternative route to this product comprises heating a mixture of ethyl 6,7-dimethoxy-2-aminoquinoline-3-carboxylate (1.38 g., 5.0 mM), ethyl 1-carbethoxyformimidate hydrochloride (1.82 g., 10 mM), triethylamine (5.1 g., 5.0 mM), ethanol (50 ml.) and N,N-dimethylformamide (20 ml.) on a steam bath for 17 hours. The reaction mixture is cooled and the solid which separates filtered off, triturated with hot chloroform and then recrystallized from chloroform to give 0.170 g. of product. M.P. 273°-274° C. (dec.).

Workup

  1. temperatureAn alternative route to this product comprises heating
  2. temperatureThe reaction mixture is cooled
  3. filtrationthe solid which separates filtered off
  4. customtriturated with hot chloroform
  5. customrecrystallized from chloroform
  6. customto give 0.170 g

Sources & evidence

ORD record
ord-f4295ace8bfa4d95b4b4f363c41d6886
Source dataset
uspto-grants-1977_08
Patent number
US04044134

Reaction notes

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