Ammonia → 7-Acetamido-4-(3-bromoanilino)-6-nitroquinazoline

HRID 1489587Notes

Reaction equation

HRID 1489587 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[NH:5]O.[N+](C1C=C2C(=CC=1)N=CN=C2)([O-])=O.[C:23]([NH:26][C:27]1[CH:36]=[C:35]2[C:30]([C:31](=O)[NH:32][CH:33]=[N:34]2)=[CH:29][C:28]=1[N+:38]([O-:40])=[O:39])(=[O:25])[CH3:24].BrC1C=C(C=CC=1)N.Cl.N>O=P(Cl)(Cl)Cl.C(O)(C)C>[C:23]([NH:26][C:27]1[CH:36]=[C:35]2[C:30]([C:31]([NH:5][C:4]3[CH:7]=[CH:8][CH:9]=[C:2]([Br:1])[CH:3]=3)=[N:32][CH:33]=[N:34]2)=[CH:29][C:28]=1[N+:38]([O-:40])=[O:39])(=[O:25])[CH3:24]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 115623-BromoanilineHCID 1317202553-Bromoanilinol 6-nitroquinazolineHCID 1356184917-acetamido-6-nitro-3H-quinazolin-4-one

Product 1

HCID 53282177-Acetamido-4-(3-bromoanilino)-6-nitroquinazolineYield 45%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 24813Phosphorus oxychlorideSolvent

Procedure

7-Acetamido-4-(3-bromoanilinol-6-nitroquinazoline. A solution of 7-acetamido-6-nitro-3H-quinazolin-4-one (5.00 g, 20 mmol) in POCl3 (250 mL) is heated under reflux for 2 h, the excess of POCl3 is removed under vacuum, and the residue is dissolved in CH2Cl2 and washed with aqueous Na2CO3 solution. Workup gives the crude 4-chloro derivative, which is coupled directly with 3-bromoaniline in isopropanol as above, and the resulting hydrochloride is converted directly to the free base, by treatment with aqueous NH3, to give 7-acetamido-4-(3-bromoanilino)-6-nitroquinazoline (3.60 g, 45%). 1H NMR (DMSO) δ10.56 (1H, s), 10.29 (1H, s), 9.34 (1H, s), 8.70 (1H, s), 8.19 (1H, brs), 7.97 (1H, s), 7.88 (1H, d, J=6.0 Hz), 7.43-7.35 (2H, m), 2.13 (3H, s).

Workup

  1. temperatureunder reflux for 2 h
  2. customthe excess of POCl3 is removed under vacuum
  3. dissolutionthe residue is dissolved in CH2Cl2
  4. washwashed with aqueous Na2CO3 solution
  5. customWorkup gives the crude 4-chloro derivative, which

Sources & evidence

ORD record
ord-da549ea129704d66b146f7bf982c900b
Source dataset
uspto-grants-1997_10
Patent number
US05679683

Reaction notes

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