Acetic Acid → 3-Amino-9-bromobenzo[f]quinazolin-1(2H)-one

HRID 1377045Notes

Reaction equation

HRID 1377045 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:14]=[CH:13][C:12]3[N:11]=[C:10]([NH:15]C(=O)C(C)(C)C)[NH:9][C:8](=[O:22])[C:7]=3[C:6]=2[CH:23]=1.C(O)(=O)C>[OH-].[Na+]>[NH2:15][C:10]1[NH:9][C:8](=[O:22])[C:7]2[C:6]3[CH:23]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=3[CH:14]=[CH:13][C:12]=2[N:11]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 135838104N-(9-bromo-1,2-dihydro-1-oxobenzo[f]quinazolin-3-yl)pivalamide

Product 1

HCID 1354229133-Amino-9-bromobenzo[f]quinazolin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
75 °C

Procedure

A solution of N-(9-bromo-1,2-dihydro-1-oxobenzo[f]quinazolin-3-yl)-pivalamide (0.15 g, 0.4 mmole) in 0.75N NaOH (7 ml) was stirred and heated to 75° C. under a nitrogen atmosphere for 10.5 hours. The solution was cooled and made slightly acidic with acetic acid to cause precipitation of the product. The precipitate was collected, washed successively with water, methanol and ether, and dried to give 3-amino-9-bromobenzo[f]quinazolin 1(2H)-one as an off-white solid. (0.115 g, 99%) 1H NMR (DMSO-d6, 200 MHz) δ: 6.64(br s, 2H, NH2); 7.31(d, J=8.8 Hz, 1H, Ar); 7.57(dd, J=8.5, 1.9 Hz, 1H, Ar); 7.83(d, J=8.6 Hz, 1H, Ar); 8.02(d, J=9.0 Hz, 1H, Ar); 9.83(s, H, Ar); 11.28(br s, 1H, NH).

Workup

  1. temperatureThe solution was cooled
  2. customprecipitation of the product
  3. customThe precipitate was collected
  4. washwashed successively with water, methanol and ether
  5. customdried

Sources & evidence

ORD record
ord-c186af750fe24c1891843b52082a66c0
Source dataset
uspto-grants-1997_09
Patent number
US05663337

Reaction notes

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