Sodium Hydroxide → 3,10-diamino-9-bromobenzo[f]quinazolin-1(2H)-one

HRID 1377052Notes

Reaction equation

HRID 1377052 reaction equation
[NH2:1][C:2]1[C:7]2[C:8]3[C:9](=[O:23])[NH:10][C:11]([NH:16]C(=O)C(C)(C)C)=[N:12][C:13]=3[CH:14]=[CH:15][C:6]=2[CH:5]=[CH:4][C:3]=1[Br:24].[OH-].[Na+].NC1NC(=O)C2C3C=C(Br)C=CC=3C=CC=2N=1>>[NH2:16][C:11]1[NH:10][C:9](=[O:23])[C:8]2[C:7]3[C:2]([NH2:1])=[C:3]([Br:24])[CH:4]=[CH:5][C:6]=3[CH:15]=[CH:14][C:13]=2[N:12]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 1354229133-Amino-9-bromobenzo[f]quinazolin-1(2H)-oneHCID 135838115N-(10-amino-9-bromo-1,2-dihydro-1-oxobenzo[f]quinazolin-3-yl)pivalamide

Product 1

HCID 1358381253,10-diamino-9-bromobenzo[f]quinazolin-1(2H)-one

Procedure

N-(10-Amino-9-bromo-1,2-dihydro-1-oxobenzo[f]quinazolin-3-yl)pivalamide (0.58 g, 1.5 mmoles) was reacted with aqueous sodium hydroxide as described for the analogous 9-bromo compound (example 2). The product was precipitated from the reaction mixture with acetic acid, filtered and washed with water to give 3,10-diamino-9-bromobenzo[f]quinazolin-1(2H)-one as a yellow solid. (0.36 g, 80%) 1H NMR (DMSO-d6, 200 MHz) δ: 6.49(br s, 2H, NH2); 6.69(br s, 1H, NH2); 7.09(d, J=8.4 Hz, 1H, Ar); 7.22(d, J=8.9 Hz, 1H, Ar); 7.56(d, J=8.4 Hz, 1H, Ar); 7.90(d, J=8.9 Hz, 1H, Ar); 11.47(br s, 1H, NH).

Workup

  1. customThe product was precipitated from the reaction mixture with acetic acid
  2. filtrationfiltered
  3. washwashed with water

Sources & evidence

ORD record
ord-883248124c2a40c395682397c770bb90
Source dataset
uspto-grants-1997_09
Patent number
US05663337

Reaction notes

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