Carbon Tetrachloride → 8-Bromomethyl-4-[(3-bromophenyl)-N-acetylamino]-6-nitro-3-quinolinecarbonitrile

HRID 1934973Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1934973
[Br:1][C:2]1[CH:3]=[C:4]([N:8]([C:12]2[C:21]3[C:16](=[C:17]([CH3:25])[CH:18]=[C:19]([N+:22]([O-:24])=[O:23])[CH:20]=3)[N:15]=[CH:14][C:13]=2[C:26]#[N:27])[C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.[Br:28]N1C(=O)CCC1=O.C(Cl)(Cl)(Cl)Cl.S(=O)(O)[O-].[Na+]>C(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:28][CH2:25][C:17]1[CH:18]=[C:19]([N+:22]([O-:24])=[O:23])[CH:20]=[C:21]2[C:16]=1[N:15]=[CH:14][C:13]([C:26]#[N:27])=[C:12]2[N:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)[C:9](=[O:11])[CH3:10]

Komponenten

7

Edukt 4

HCID 5943Carbon TetrachlorideHCID 67184N-bromobutanimideHCID 224667474-[(3-Bromophenyl)-N-acetylamino]-8-methyl-6-nitro-3-quinolinecarbonitrileHCID 23665763Sodium Bisulfite

Produkt 1

HCID 224666528-Bromomethyl-4-[(3-bromophenyl)-N-acetylamino]-6-nitro-3-quinolinecarbonitrileAusbeute 119 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7187Benzoyl PeroxideKatalysator2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A stirred mixture of 4-[(3-bromophenyl)-N-acetylamino]-8-methyl-6-nitro-3-quinolinecarbonitrile (10.6 g, 25 mmol), N-bromosuccinimide (6.68 g, 37.5 mmol), 0.30 g of dibenzoyl peroxide, and 200 ml of carbon tetrachloride was refluxed for 2 h, treated with an additional 0.30 g of dibenzoyl peroxide, and refluxed an additional 2.5 h, cooled, diluted with methylene chloride, and stirred with aqueous sodium bisulfite. The organic layer was separated and washed successively with water, sodium bicarbonate solution, and water. The solution was dried and evaporated to give 15 g of a white foam, NMR (CDCl3) δ 5.19 (dd, CH2Br).

Aufarbeitung

  1. temperaturewas refluxed for 2 h
  2. temperaturerefluxed an additional 2.5 h
  3. temperaturecooled
  4. customThe organic layer was separated
  5. washwashed successively with water, sodium bicarbonate solution, and water
  6. customThe solution was dried
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-5252d63abc6c41a190def99fc74c7167
Quelldatensatz
uspto-grants-2002_05
Patentnummer
US06384051B1

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