Carbon tetrabromide → 3-Bromomethyl-8-(2,6-dichlorobenzoylamino)quinoline

HRID 613486Notes

Reaction equation

HRID 613486 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][C:13]([CH2:17]O)=[CH:12]2)=[O:5].C(Br)(Br)(Br)[Br:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Br:25][CH2:17][C:13]1[CH:14]=[N:15][C:16]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][C:7]=2[NH:6][C:4](=[O:5])[C:3]1[C:2]([Cl:1])=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:23]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 195922958-(2,6-Dichlorobenzoylamino)-3-hydroxymethylquinoline

Product 1

HCID 195923883-Bromomethyl-8-(2,6-dichlorobenzoylamino)quinolineYield 71.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8-(2,6-dichlorobenzoylamino)-3-hydroxymethylquinoline (300 mg) in tetrahydrofuran were added carbon tetrabromide (573 mg) and triphenylphosphine (453 mg), and the mixture was stirred for 30 minutes at ambient temperature. Insoluble material was filtered off, and the filtrate was evaporated in vacuo. The residue was purified by column chromatography on silica gel (dichloromethane) to give 3-bromomethyl-8-(2,6-dichlorobenzoylamino)quinoline (253.4 mg).

Workup

  1. filtrationInsoluble material was filtered off
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was purified by column chromatography on silica gel (dichloromethane)

Sources & evidence

ORD record
ord-2c27eaad265041d6a1f136f7533522fc
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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