Propylamine → 2-Ethyl-3-propylquinazolin-4(3H)-one

HRID 238194Notes

Reaction equation

HRID 238194 reaction equation
[CH2:1]([C:3]1O[C:5](=[O:13])[C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[N:8]=1)[CH3:2].[CH2:14]([NH2:17])[CH2:15][CH3:16]>>[CH2:1]([C:3]1[N:17]([CH2:14][CH2:15][CH3:16])[C:5](=[O:13])[C:6]2[C:7](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:8]=1)[CH3:2]

Participants

3

Reactant 2

HCID 7852PropylamineHCID 9285262-Ethyl-benzo[d][1,3]oxazin-4-one

Product 1

HCID 5291112-Ethyl-3-propylquinazolin-4(3H)-oneYield 29.1%

Conditions

Temperature
110 °C

Procedure

A mixture of 2-ethyl-benzo[d][1,3]oxazin-4-one (541 mg, 3.1 mmol) and propylamine (254 μL, 3.1 mmol) were heated to 110° C. for 1 hour. The crude product was purified by column chromatography (10-40% ethyl acetate-hexanes) to yield the product as a white solid (195 mg, 29%). 1H NMR (CDCl3) δ 1.03 (t, 3H, J=7.4 Hz), 1.41 (t, 3H, J=7.3 Hz), 1.76 (sex, 2H, J=7.7 Hz), 2.86 (q, 2H, J=7.4 Hz), 4.05 (t, 2H, J=7.9 Hz), 7.42 (t, 1H, J=8.1 Hz), 7.63 (d, 1H, J=7.7 Hz), 7.70 (t, 1H, J=7.7 Hz), 8.24 (d, 1H, J=8.1 Hz).

Workup

  1. customThe crude product was purified by column chromatography (10-40% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-93282f27c7324c43b9574405a79f830f
Source dataset
uspto-grants-2014_02
Patent number
US08642609B2

Reaction notes

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