Diphenyl Ether → Ethyl 4-Oxo-4H-pyrimido[2,1-a]isoquinoline-3-carboxylate

HRID 1704810Notes

Reaction equation

HRID 1704810 reaction equation
[C:1]1([NH:11][CH:12]=[C:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14](OCC)=[O:15])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.C1(OC2C=CC=CC=2)C=CC=CC=1>>[O:15]=[C:14]1[N:2]2[CH:3]=[CH:4][C:5]3[C:10]([C:1]2=[N:11][CH:12]=[C:13]1[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:9][CH:8]=[CH:7][CH:6]=3

Participants

3

Reactant 2

HCID 7583Diphenyl EtherHCID 22758864Diethyl Isoquinolylaminomethylenemalonate

Product 1

HCID 13851097Ethyl 4-Oxo-4H-pyrimido[2,1-a]isoquinoline-3-carboxylateYield 83%

Procedure

A stirred mixture of diethyl isoquinolylaminomethylenemalonate (32.0 g., 0.0986 mole) and diphenyl ether (125 ml.) under nitrogen was heated at a temperature of 235° for 15 minutes. The solid, m.p. 183°-184°, obtained upon cooling and dilution with Skellysolve B was recrystallized from ethanol to give salmon crystals (22 g., 83% yield), m.p. 189°-191°. An analytical sample, recrystallized from ethanol, had m.p. 190°-192°.

Workup

  1. temperaturewas heated at a temperature of 235° for 15 minutes
  2. customThe solid, m.p. 183°-184°, obtained
  3. temperatureupon cooling
  4. customdilution with Skellysolve B was recrystallized from ethanol
  5. customto give salmon crystals (22 g., 83% yield), m.p. 189°-191°
  6. customAn analytical sample, recrystallized from ethanol

Sources & evidence

ORD record
ord-27f349c77d9f47dbb268484e4a0f19f3
Source dataset
uspto-grants-1978_11
Patent number
US04127720

Reaction notes

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