Dichloromethane → HCID 136404540, compound

HRID 981920Notes

Reaction equation

HRID 981920 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:16]=1[C:15]([NH2:17])=[C:14]1[C:9]([CH2:10][CH2:11][CH2:12][CH2:13]1)=[N:8]2.B(Br)(Br)Br.[Cl:22]CCl>>[ClH:22].[OH:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:16]=1[C:15]([NH2:17])=[C:14]1[C:9]([CH2:10][CH2:11][CH2:12][CH2:13]1)=[N:8]2

Participants

4

Reactant 3

HCID 6344Dichloromethane2×HCID 25134Boron tribromideHCID 197702928-Methoxy-1,2,3,4-tetrahydro-9-acridinamine

Product 1

HCID 136404540HCID 136404540, compoundYield 61%

Procedure

8-Methoxy-1,2,3,4-tetrahydro-9-acridinamine (4.0 g) was dissolved in dichloromethane (76 ml). Boron tribromide in dichloromethane (15.0 ml of a 1.0M solution) was added, and the reaction mixture was stirred 1 hr and then concentrated under reduced pressure. The residue was dissolved in warm water (100 ml), concentrated hydrochloric acid (400 ml) was added and the solution was chilled overnight in the refrigerator. The salt was collected and recrystallized from methanol-ether to give 2.68 g (61%) of product, mp 270° C. (dec).

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in warm water (100 ml)
  3. additionconcentrated hydrochloric acid (400 ml) was added
  4. temperaturethe solution was chilled overnight in the refrigerator
  5. customThe salt was collected
  6. customrecrystallized from methanol-ether

Sources & evidence

ORD record
ord-bef5a7abc7ce49c6942efc562d734be5
Source dataset
uspto-grants-1991_02
Patent number
US04994452

Reaction notes

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