Pyridine → HCID 135838164, compound

HRID 2258660Notes

Reaction equation

HRID 2258660 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-74cf662c01ff4a879894286d53f7b203
Source dataset
uspto-grants-1997_08
Patent number
US05661155

Reaction notes

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