Bromine → HCID 13376761, compound

HRID 462507Notes

Reaction equation

HRID 462507 reaction equation
[Br:1]N1C(=O)CCC1=O.[Br:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]1[CH2:19][CH2:20][CH2:21][C:22](=[O:23])[C:14]1=[C:13]2[CH3:24].BrBr>C(Cl)Cl>[Br:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]1[CH2:19][CH2:20][CH:21]([Br:1])[C:22](=[O:23])[C:14]1=[C:13]2[CH3:24]

Participants

5

Reactant 3

HCID 24408BromineHCID 67184N-bromobutanimideHCID 13376760HCID 13376760, compound

Product 1

HCID 13376761HCID 13376761, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Aged N-bromosuccinimide (4.89 g, 27.5 mmol) was added in small portions (over 15 min) to a solution of 2-bromo-10-methyl-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-one (described in Example 8, 5.0 g) in methylene chloride (100 mL) and stirring at room temperature was continued for 30 min. This crude mixture was then protected against light, and a solution of bromine (2 mL) in methylene chloride (200 mL) was added very slowly from a dropping funnel. The reaction mixture was washed successively with cold water, 5% sodium bicarbonate, and water again. After drying (MgSO4) and filtration, the solvent was evaporated, and the title compound was crystallized from chloroform, mp 156° C.; yield 6.6 g; Anal. Calcd for C13H11Br2NO: C, 43.72% H, 3.10% N, 3.92% and Found: C, 43.35% H, 3.00% N, 3.99%.

Workup

  1. additionwas added very slowly from a dropping funnel
  2. washThe reaction mixture was washed successively with cold water, 5% sodium bicarbonate, and water again
  3. customAfter drying
  4. filtration(MgSO4) and filtration
  5. customthe solvent was evaporated
  6. customthe title compound was crystallized from chloroform, mp 156° C.

Sources & evidence

ORD record
ord-4dfd30e928884a6ead85bf5ff48f4b99
Source dataset
uspto-grants-1985_05
Patent number
US04515949

Reaction notes

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