Ethyl 2-pyridinecarboxylate → HCID 14508407, compound

HRID 2052370Notes

Reaction equation

HRID 2052370 reaction equation
[CH3:1][C:2]1[N:11]([C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=2)[C:10](=[O:19])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26](OCC)=[O:27].[H-].[Na+].[K+].[Br-]>C1COCC1>[O:27]=[C:26]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][N:20]=1)[CH2:1][C:2]1[N:11]([C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=2)[C:10](=[O:19])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

6

Reactant 4

HCID 17307Ethyl 2-pyridinecarboxylateHCID 24758Sodium hydrideHCID 633773-(4-bromophenyl)-2-methylquinazolin-4(3H)-oneHCID 253877Potassium Bromide

Product 1

HCID 14508407HCID 14508407, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Treatment of 3.15 g (10 mmol) of 2-methyl-3-p-bromophenyl-4(3H)-quinazolinone and 1.81 g (12 mmol) of ethyl picolinate with 1.92 g (40 mmol) of sodium hydride (50%) in 160 ml of THF for a reaction period of 2.5 hours resulted in a yellow-brown reaction slurry which was processed using Method B. The crude yellow product was recrystallized from dimethyl sulfoxide-acetone to yield 4.06 g (96%) of yellow microcrystals, mp 312°-313° (dec): 1H NMR (CDCl3 with 3 drops CF3CO2H) δ 8.96-7.11 (m, 12H, aromatic) and 5.50 ppm (s, 1H, vinyl); ir (KBr) 1685 cm-1C=O).

Workup

  1. customresulted in a yellow-brown reaction slurry which
  2. customThe crude yellow product was recrystallized from dimethyl sulfoxide-acetone
  3. customto yield 4.06 g (96%) of yellow microcrystals, mp 312°-313° (dec)

Sources & evidence

ORD record
ord-5c7cac69e9ca41f99e5eecea842e4885
Source dataset
uspto-grants-1980_01
Patent number
US04183931

Reaction notes

Loading…