Pyridine → HCID 135838164, compound

HRID 381559Notes

Reaction equation

HRID 381559 reaction equation
[Br:1][C:2]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][C:5]2[C:6]3[C:7](=[O:21])[NH:8][C:9]([NH:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])=[N:10][C:11]=3[CH2:12][CH2:13][C:4]=2[CH:3]=1.BrN1C(=O)CCC1=O.N1C=CC=CC=1>C1C=CC=CC=1>[Br:1][C:2]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][C:5]2[C:6]3[C:7](=[O:21])[NH:8][C:9]([NH:14][C:15](=[O:20])[C:16]([CH3:18])([CH3:19])[CH3:17])=[N:10][C:11]=3[CH:12]=[CH:13][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 67184N-bromobutanimideHCID 135838149HCID 135838149, compound

Product 1

HCID 135838164HCID 135838164, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

N-(8-Bromo-1,2,5,6-tetrahydro-9-nitro-1-oxobenzo[f]quinazolin-3-yl)pivalamide (0.23 g, 0.5 mmole) was reacted with N-bromosuccinimide (0.12 g, 0.7 mmole) and pyridine (0.06 ml, 0.8 mmole) in dry benzene (150 ml) in the same manner as in example 2. The crude product was purified by trituration with methanol:water (1:9), followed by filtration and washing (water and methanol) to give, after drying, N-(8-bromo-1,2-dihydro-9-nitro-1-oxobenzo[f]quinazolin-3-yl)pivalamide as a pale yellow solid. (0.20 g, 94%) 1H NMR(DMSO-d6, 200 MHz) δ: 1.27(s, 9H, t-butyl); 7.76(d, J=9.0 Hz, 1H, Ar); 8.32(d, J=9.0 Hz, 1H, Ar); 8.65(s, 1H, Ar); 10.21(s, 1H, Ar); 11.40(s, 1H, NH); 12.45(br s, 1H, NH).

Workup

  1. customThe crude product was purified by trituration with methanol:water (1:9)
  2. filtrationfollowed by filtration
  3. washwashing (water and methanol)
  4. customto give
  5. customafter drying

Sources & evidence

ORD record
ord-ea39b94ef75a4f2ab09720db150323ae
Source dataset
uspto-grants-2001_10
Patent number
US06306865B1

Reaction notes

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