N-bromobutanimide → Ethyl acetate hexane

HRID 1426267Notes

Reaction equation

HRID 1426267 reaction equation
[C:1]([C:5]1C=C(C2N=C(C)C3C(C=2)=C[C:17]([O:21]C)=[C:16](OC)C=3)[CH:8]=[CH:9][CH:10]=1)(C)(C)[CH3:2].[CH2:26]1[C:31](=[O:32])N(Br)C(=O)C1>C(Cl)(Cl)(Cl)Cl.CCCCCC.CC(N=NC(C#N)(C)C)(C#N)C>[CH3:16][CH2:17][O:21][C:31]([CH3:26])=[O:32].[CH3:2][CH2:1][CH2:5][CH2:10][CH2:9][CH3:8]

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 67995172HCID 67995172, compound

Product 1

HCID 21226206Ethyl acetate hexaneYield 168.4%

Reagents, catalysts & solvents 3

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolventHCID 8058HexaneSolvent

Procedure

3-(3-(tert-Butyl)phenyl)-6,7-dimethoxy-1-methylisoquinoline (400 mg), NBS (223 mg, 1.05 eq.), and AIBN (20 mg, 0.1 eq.) in 7 mL CCl4 were heated at 85° C. for 2 hours. Reaction mixture was then cooled to room temperature and diluted with hexane. Solid precipitate was filtered off and filtrate was concentrated. Chromatography achieved using ISCO max gradient 15% EtOAc/hexane yielding product as a white solid (350 mg, 71% yield). 1H NMR (400 MHz) (CDCl3) δ 8.15-8.14 (m, 1H), 7.94-7.91 (m, 2H), 7.48-7.45 (m, 3H), 7.18 9s, 1H), 5.10 (s, 2H), 4.11 (s, 3H), 4.07 (s, 3H), 1.45 (s, 9H). 13C NMR (100 MHz) (CDCl3) δ 153.03, 152.89, 151.50, 150.11, 149.96, 139.19, 134.59, 128.46, 125.45, 124.18, 123.86, 121.45, 116.56, 105.75, 103.56, 56.16, 56.10, 34.90, 32.97, 31.47.

Workup

  1. customReaction mixture
  2. filtrationSolid precipitate was filtered off
  3. concentrationfiltrate was concentrated

Sources & evidence

ORD record
ord-a4b6ba7c0eaf43b2aa7535b384cde7ba
Source dataset
uspto-grants-2015_01
Patent number
US08933096B2

Reaction notes

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