4-Fluoroaniline → HCID 178523230, compound

HRID 2185197Notes

Reaction equation

HRID 2185197 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:18]=[C:17]([OH:19])[C:16]3[C:11](=[C:12]([C:23](OC)=[O:24])[CH:13]=[C:14]([N+:20]([O-:22])=[O:21])[CH:15]=3)[N:10]=2)=[CH:4][CH:3]=1.ClC1[N:37]=[C:36](O)[C:35]2[C:30](=[C:31]([C:42](OC)=O)C=[C:33]([N+:39]([O-])=O)[CH:34]=2)N=1.FC1C=CC(N)=CC=1>CN1CCCC1=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:18]=[C:23]([OH:24])[C:12]3[C:11](=[C:16]([C:17]([NH:39][CH2:33][CH2:34][C:35]4[CH:36]=[N:37][CH:42]=[CH:31][CH:30]=4)=[O:19])[CH:15]=[C:14]([N+:20]([O-:22])=[O:21])[CH:13]=3)[N:10]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 97314-FluoroanilineHCID 178498466HCID 178498466, compoundHCID 178498467HCID 178498467, compound

Product 1

HCID 178523230HCID 178523230, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Methyl 2-(4-fluorophenyl)amino-4-hydroxy-6-nitroquinazoline-8-carboxylate. A solution of methyl 2-chloro-4-hydroxy-6-nitroquinazoline-8-carboxylate (1.50 g) and 4-fluoroaniline (1.76 g) in N-methylpyrrolidone (30 mL) was heated to 100° C. for 1 h. After cooling to room temperature, the reaction was cooled to 0° C. and a precipitate formed. The precipitate was isolated by filtration and washed with water (100 mL), 1M HCl (100 mL), and water (100 mL). The resulting material was dried to afford the title compound as a yellow solid (1.89 g). 1H NMR (300 MHz, DMSO-d6 (w/TFA (50 uL)): 8.80 (d, J=2.6 Hz, 1H), 8.69 (d, J=2.2 Hz, 1H), 7.85 (dd, J=8.4, 5.3 Hz, 2H), 7.24 (t, J=8.7 Hz, 2H), 3.97 (s, 3H). HPLC (Method F): 6.71 min. MS (APCI+): m/z 359.

Workup

  1. temperaturethe reaction was cooled to 0° C.
  2. customa precipitate formed
  3. customThe precipitate was isolated by filtration
  4. washwashed with water (100 mL), 1M HCl (100 mL), and water (100 mL)
  5. customThe resulting material was dried

Sources & evidence

ORD record
ord-ca9380845599447984b0a66b9b291f28
Source dataset
uspto-grants-2002_06
Patent number
US06399603B1

Reaction notes

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