Sodium Hydroxide → 3-(4-Amino-2-bromophenyl) 1,3-dihydroquinazoline-2,4-dione

HRID 1437564Notes

Reaction equation

HRID 1437564 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[N:11]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][C:12]1=[O:22].O.O.[Sn](Cl)Cl.[OH-].[Na+]>C(OCC)(=O)C>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([N:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][C:12]2=[O:22])=[C:2]([Br:1])[CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 220644013-(2-Bromo-4-nitrophenyl)-1,3-dihydroquinazoline-2,4-dione

Product 1

HCID 220643833-(4-Amino-2-bromophenyl) 1,3-dihydroquinazoline-2,4-dioneYield 94%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of 3-(2-bromo-4-nitrophenyl)-1,3-dihydroquinazoline-2,4-dione (0.18 g, 0.5 mmol) and tin(II) chloride dihydrate (0.45 g, 2.0 mmol) in ethyl acetate (5 mL) was heated at 70° C. for 4 hr. The reaction mixture was then cooled, mixed with Celite, made basic with 4N NaOH (3 mL), filtered through Celite, and concentrated in vacuo to give the desired compound (0.155 g, 94%). ES-MS (M+H)+=332, 334 (Br).

Workup

  1. temperatureThe reaction mixture was then cooled
  2. additionmixed with Celite
  3. filtrationfiltered through Celite
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-734dacc7e615407a9081506156badd82
Source dataset
uspto-grants-2009_11
Patent number
US07622474B2

Reaction notes

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