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

HRID 1358270Notes

Reaction equation

HRID 1358270 reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9](=O)[NH:10][CH:11]=[N:12]2)=[CH:7][C:6]=1[N+:16]([O-:18])=[O:17])(=[O:3])[CH3:2].[Br:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][CH:26]=1)[NH2:23].Cl.N>O=P(Cl)(Cl)Cl.C(O)(C)C>[C:1]([NH:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([NH:23][C:22]3[CH:24]=[CH:25][CH:26]=[C:20]([Br:19])[CH:21]=3)=[N:10][CH:11]=[N:12]2)=[CH:7][C:6]=1[N+:16]([O-:18])=[O:17])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 115623-BromoanilineHCID 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

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-f31f5c4a8e9b43389aa01b63ddbd64df
Source dataset
uspto-grants-2003_07
Patent number
US06596726B1

Reaction notes

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