Ammonia → N-(10)-Ethylquinazoline

HRID 238232Notes

Reaction equation

HRID 238232 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10](=O)[CH2:11][CH3:12])=O.[NH3:14]>>[CH2:11]([C:10]1[N:14]=[CH:1][C:3]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:9]=1)[CH3:12]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 220743032-(Propanoylamino)benzaldehyde

Product 1

HCID 3080902N-(10)-EthylquinazolineYield 100%

Conditions

Temperature
100 °C

Procedure

N-(2-Formyl-phenyl)-propionamide (1.65 g, 9.3 mmol) was combined with ammonia (24 mL, 2M solution in methanol) in a flask fitted with a condenser and stopper with a needle to vent. The reaction was heated to 100° C. for 1 day. The reaction mixture was concentrated in vacuo to yield the crude product as an orange oil (1.47 g, 100%). This product was used without further purification. 1H NMR (400 MHz, CDCl3) δ 9.36 (s, 1H), 7.99 (d, J=10.0 Hz, 1H), 7.89 (m, 2H), 7.60 (t, J=8.1 Hz, 1H), 3.16 (q, J=7.6 Hz, 2H), 1.47 (t, J=7.6 Hz, 3H); HPLC ret. time 0.61 min, 10-99% CH3CN, 5 min run; ESI-MS m/z 159.0 (MH+).

Workup

  1. customfitted with a condenser
  2. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-7182585407d643bd924c3ae8a15a4bb2
Source dataset
uspto-grants-2014_02
Patent number
US08642609B2

Reaction notes

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