Pyridine → HCID 135838164, compound

HRID 1654354Notes

Reaction equation

HRID 1654354 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-fd6ee30403b443e2bdf51dc2ce1f2a54
Source dataset
uspto-grants-1995_04
Patent number
US05405851

Reaction notes

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