ethyl 1H-pyrazole-4-carboxylate → 1-(6-nitro-4-oxo-3,4-dihydro-quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 1428871Notes

Reaction equation

HRID 1428871 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:3]=[N:2]1.Cl[C:12]1[NH:21][C:20](=[O:22])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([N+:23]([O-:25])=[O:24])[CH:18]=2)[N:13]=1>>[CH2:9]([O:8][C:6]([C:4]1[CH:5]=[N:1][N:2]([C:12]2[NH:21][C:20](=[O:22])[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([N+:23]([O-:25])=[O:24])[CH:18]=3)[N:13]=2)[CH:3]=1)=[O:7])[CH3:10]

Participants

3

Reactant 2

HCID 142179ethyl 1H-pyrazole-4-carboxylateHCID 1356751542-Chloro-6-nitroquinazolin-4(1H)-one

Product 1

HCID 1363371881-(6-nitro-4-oxo-3,4-dihydro-quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid ethyl esterYield 98%

Conditions

Temperature
130 °C

Procedure

Ethyl pyrazole-4-carboxylate (1.83 g, 13.1 mmol) was added to a suspension of 2-chloro-6-nitro-3H-quinazolin-4-one (2.95 g, 13.1 mmol) in xylenes (52 mL). The reaction mixture was heated to 130° C. for 1 h, allowed to cool, and stirred at room temperature for 18 h. The precipitate was collected and rinsed with ether (20 mL) to yield the titled compound (4.22 g, 98%). MS (ESI/Cl): mass calcd. for C14H11N5O5, 329.1; m/z found, 330.1 [M+H]+.

Workup

  1. temperatureto cool
  2. customThe precipitate was collected
  3. washrinsed with ether (20 mL)

Sources & evidence

ORD record
ord-c9e7633c41184076b95363f596ddcbbd
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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