Pyridine → HCID 135838164, compound

HRID 1377054Notes

Reaction equation

HRID 1377054 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-7ea45b9dbd7a453c8d12afd585318117
Source dataset
uspto-grants-1997_09
Patent number
US05663337

Reaction notes

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