Iodoethane → HCID 15675260, compound

HRID 1090141Notes

Reaction equation

HRID 1090141 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][CH3:10])[NH2:5].C([O:13][CH:14]=[C:15]([C:21](OCC)=O)[C:16]([O:18][CH2:19][CH3:20])=[O:17])C.[CH:26](/C1C(O)=C(OC)C=C2C=1NC=CC2=O)=[CH:27]\CC.C(=O)([O-])[O-].[K+].[K+].C(I)C>C1(OC2C=CC=CC=2)C=CC=CC=1.CCOCC>[CH2:26]([O:1][C:2]1[CH:3]=[C:4]2[C:6]([C:14](=[O:13])[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:21][NH:5]2)=[CH:7][C:8]=1[O:9][CH3:10])[CH3:27]

Participants

8

Reactant 5

HCID 6340IodoethaneHCID 6871Diethyl (ethoxymethylene)malonateHCID 11430Potassium CarbonateHCID 743145-Amino-2-methoxyphenolHCID 86745380HCID 86745380, compound

Product 1

HCID 15675260HCID 15675260, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 7583Diphenyl EtherSolvent

Procedure

3-Hydroxy-4-methoxyaniline (10.0 g) and diethyl ethoxymethylenemalonate (17.0 g) were condensed in the same manner as in the preparation of compound 72. The condensation product was O-ethylated with potassium carbonate (15.0 g) and ethyl iodide (7.0 ml) and then heated in diphenyl ether (70 ml) at a temperature of 240°-250° for 3 hours. After the mixture was left to cool, ether was added to the mixture. The resulting precipitate was collected by filtration, washed with water and dried to give 7-ethoxy-3-ethoxycarbonyl-6-methoxy-4(1H)-quinolone (10.2 g). The compound (5.0 g) was subjected to N-methylation and hydrolysis in the same manner as in Experimental Example 9 to obtain 3-carboxyl-7-ethoxy-6-methoxy-1-methyl-4(1H)-quinolone (compound 92, 4.4 g).

Workup

  1. customcondensed in the same manner
  2. waitAfter the mixture was left
  3. temperatureto cool
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-aead8a8cea9043b787cf480f1e80a837
Source dataset
uspto-grants-1992_01
Patent number
US05081121

Reaction notes

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