Carbon tetrabromide → HCID 19356218, compound

HRID 377618Notes

Reaction equation

HRID 377618 reaction equation
O[CH2:2][CH2:3][NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:7](=[O:21])[C:6]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23].C(Br)(Br)(Br)[Br:28].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Br:28][CH2:2][CH2:3][NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:7](=[O:21])[C:6]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 19356233HCID 19356233, compound

Product 1

HCID 19356218HCID 19356218, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolved in 30 ml of tetrahydrofuran were 0.352 g (1 mmol) of ethyl 4-(2-hydroxyethylamino)-2-oxo-1-phenyl-1,2-dihydroquinoline-3-carboxylate, 0.67 g (2 mmol) of carbon tetrabromide and 0.531 g (2 mmol) of triphenylphosphine, followed by a reaction at room temperature for 5 hours. The insoluble matter was filtered off, and the organic layer was concentrated under reduced pressure. The resulting residue was purified by chromatography on a silica gel column and then recrystallized from ethyl acetate/isopropyl ether, whereby 0.31 g of ethyl 4-(2-bromoethylamino)-2-oxo-1-phenyl-1,2-dihydroquinoline-3-carboxylate was obtained (yield: 74.7%).

Workup

  1. customfollowed by a reaction at room temperature for 5 hours
  2. filtrationThe insoluble matter was filtered off
  3. concentrationthe organic layer was concentrated under reduced pressure
  4. customThe resulting residue was purified by chromatography on a silica gel column
  5. customrecrystallized from ethyl acetate/isopropyl ether

Sources & evidence

ORD record
ord-646147a89d954e40a9d0ae922c6fe3e0
Source dataset
uspto-grants-2000_02
Patent number
US06028081

Reaction notes

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