Sodium Hydroxide → HCID 135838175, compound

HRID 381560Notes

Reaction equation

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

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 135838208HCID 135838208, compound

Product 1

HCID 135838175HCID 135838175, compound

Procedure

N-(9-Amino-1,2-dihydro-1-oxobenzo[f]quinazolin-3-yl)pivalamide (0.065 g, 0.2 mmole) was reacted with aqueous sodium hydroxide in the same manner as in example 2. The product was precipitated from the basic reaction mixture with acetic acid, filtered and washed with water to give 3,9-diaminobenzo[f]quinazolin-1(2H)-one as a tan solid. (0.04 g, 84%) 1H NMR(DMSO-d6, 300 MHz) δ: 5.54(br s, 2H, NH2); 6.35(br s, 2H, NH2); 6.80(dd, J=8.5, 2.3 Hz, 1H, Ar); 6.87(d, J=8.6 Hz, 1H, Ar); 7.52(d, J=8.6 Hz, 1H, Ar); 7.73(d, J=8.6 Hz, 1H, Ar); 8.73(s, 1H, Ar); 10.91(br s, 1H, NH).

Workup

customThe product was precipitated from the basic reaction mixture with acetic acid
filtrationfiltered
washwashed with water

Sources & evidence

ORD record: ord-4c09e571c99a405b920c3de478bf3e36
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06306865B1

Reaction notes

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