Triethylamine → ethyl 6-hydroxy-4-oxo-1H-quinazoline-2-carboxylate

HRID 1162996Notes

Reaction equation

HRID 1162996 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.C(N(CC)CC)C.[CH2:19]([O:21][C:22](=[O:28])[C:23](OCC)=[NH:24])[CH3:20]>C(O)C>[CH2:19]([O:21][C:22]([C:23]1[N:24]=[C:4]([OH:6])[C:3]2[C:2](=[CH:10][CH:9]=[C:8]([OH:11])[CH:7]=2)[N:1]=1)=[O:28])[CH3:20]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 1645925-Hydroxyanthranilic acidHCID 10920638Ethyl 2-ethoxy-2-iminoacetate

Product 1

HCID 178470314ethyl 6-hydroxy-4-oxo-1H-quinazoline-2-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

2-amino-5-hydroxy-benzoic acid (15 mmol) are suspended in ethanol (water free, 600 ml) and heated up to 60° C. and stirred. Then triethylamine (30 mmol) is added and a clear solution is formed. Ethoxy-imino-acetic acid ethyl ester (16.5 mmol) is added at 60° C. and after 15 minutes another portion of triethylamine (15 mmol) is added and the mixture stirred for another 30 minutes. The mixture is cooled down to RT and left at RT without stirring over night. The solid material formed was filtered off, washed with ethanol/ether and dried (vacuum). A pale brown powder with mp. 258-260° C. (decomposition) is obtained.

Workup

  1. customa clear solution is formed
  2. additionis added
  3. stirringthe mixture stirred for another 30 minutes
  4. temperatureThe mixture is cooled down to RT
  5. waitleft at RT
  6. stirringwithout stirring over night
  7. customThe solid material formed
  8. filtrationwas filtered off
  9. washwashed with ethanol/ether
  10. customdried (vacuum)
  11. customA pale brown powder with mp. 258-260° C. (decomposition) is obtained

Sources & evidence

ORD record
ord-3890eacfac754a66a6c81230f894be3a
Source dataset
uspto-grants-2010_10
Patent number
US07820818B2

Reaction notes

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