Hydrochloric Acid → HCID 136014317, compound

HRID 1424460Notes

Reaction equation

HRID 1424460 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([Br:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:13]([C:18]#[N:19])(=[O:17])[O:14][CH2:15][CH3:16].Cl.C(=O)([O-])O.[Na+]>CC(O)=O.O>[NH2:1][C:2]1[CH:11]=[C:10]([Br:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Br:12][C:10]1[CH:11]=[C:2]2[C:3]([C:4](=[O:6])[NH:19][C:18]([C:13]([O:14][CH2:15][CH3:16])=[O:17])=[N:1]2)=[CH:8][CH:9]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 69336Ethyl cyanoformateHCID 516892Sodium BicarbonateHCID 17871390Methyl 2-Amino-4-bromobenzoate

Product 2

HCID 17871390Methyl 2-Amino-4-bromobenzoateHCID 136014317HCID 136014317, compoundYield 115.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Methyl 2-amino-4-bromobenzoate was prepared from the corresponding acid by Fischer esterification. A mixture of methyl 2-amino-4-bromobenzoate (1.1 g, 4.8 mmol) and ethyl carbonocyanidate (0.95 g, 9.66 mmol) in HOAc (4 mL) was treated with a s12 N HCl (0.4 mL) and the resulting mixture was stirred at 70° C. for 3 h. After cooling to rt, water was added followed by addition of aq sodium hydrogen carbonate to pH ˜5. The precipitated solid was filtered and washed thoroughly with water and diethyl ether to afford ethyl 7-bromo-4-oxo-3,4-dihydroquinazoline-2-carboxylate (825 mg, 58%). 1H NMR (300 MHz, DMSO-d6) δ 2.82 (s, 1H), 8.06-8.09 (m, 2H), 7.81 (d, J=8.4 Hz, 1H), 4.38 (q, J=7.0 Hz, 2H), 1.35 (t, J=7.0 Hz, 3H); LC-MS (ESI) m/z 296 (M+H)+.

Workup

  1. temperatureAfter cooling to rt
  2. filtrationThe precipitated solid was filtered
  3. washwashed thoroughly with water and diethyl ether

Sources & evidence

ORD record
ord-3d7a6266ad774656933d5f530f8408f2
Source dataset
uspto-grants-2015_01
Patent number
US08927711B2

Reaction notes

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