Bromoacetyl bromide → 1-(Bromoacetyl)-1,2,3,4-tetrahydroquinoline

HRID 597705Notes

Reaction equation

HRID 597705 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].[NH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][CH2:7]1>C1C=CC=CC=1>[Br:1][CH2:2][C:3]([N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][CH2:7]1)=[O:4]

Participants

4

Reactant 2

HCID 61147Bromoacetyl bromideHCID 694601,2,3,4-Tetrahydroquinoline

Product 1

HCID 5838141-(Bromoacetyl)-1,2,3,4-tetrahydroquinoline

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a stirred solution of 20.2 g. of bromoacetyl bromide in 150 ml. of benzene is added dropwise over 30 minutes, 26.6 g. of 1,2,3,4-tetrahydroquinoline dissolved in 35 ml. of benzene. The reaction mixture is then stirred at room temperature for 18 hours, after which time the precipitate is filtered off. The resultant filtrate is washed successively with 1N HCL solution and with a saturated sodium chloride solution, dried, and the solvent removed under reduced pressure to yield 1-(bromoacetyl)-1,2,3,4-tetrahydroquinoline, b.p. 70°-80° C. (at 0.1 mm. Hg).

Workup

  1. filtrationafter which time the precipitate is filtered off
  2. washThe resultant filtrate is washed successively with 1N HCL solution and with a saturated sodium chloride solution
  3. customdried
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-ce6c420f2dd44392ad412c7d98e22342
Source dataset
uspto-grants-1977_03
Patent number
US04015005

Reaction notes

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