Sodium Hydroxide → HCID 10546231, compound

HRID 129777Notes

Reaction equation

HRID 129777 reaction equation
[C:1]([N:9]1[C:17]2[CH:16]=[CH:15][CH:14]=[C:13]3[CH2:18][C@@H:19]([NH2:21])[CH2:20][C@H:11]([C:12]=23)[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].[Br:27]Br.[OH-].[Na+]>C(O)(=O)C.C(OCC)C.O>[C:1]([N:9]1[C:17]2[CH:16]=[CH:15][C:14]([Br:27])=[C:13]3[CH2:18][C@@H:19]([NH2:21])[CH2:20][C@H:11]([C:12]=23)[CH2:10]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 24408BromineHCID 517045Sodium AcetateHCID 10850226HCID 10850226, compound

Product 1

HCID 10546231HCID 10546231, compoundYield 88.8%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

(2aR,4S)-1-Benzoyl-4-amino-1,2,2a,3,4,5-hexahydrobenz[cd]indole (29.4 g, 0.106 mole) was placed into a 500 ml three neck round bottom flask equipped with a mechanical stirrer, a nitrogen inlet and a constant addition funnel. The substrate was dissolved in glacial acetic acid (250 ml), and sodium acetate (34.7 g, 0.423 mole, 4 mol equiv) was then added. A solution of bromine (21.8 ml, 0.424 mole) in acetic acid was then added dropwise over a period of one hour with vigorous stirring and then stirred at room temperature overnight. The resulting thick slurry was diluted with ethyl ether, filtered and washed with ethyl ether. The material thus obtained was slurried in H2O and the pH adjusted to 11-12 with 5N NaOH. The solid was filtered, washed well with H2O and dried in vacuo to provide 33.6 g (88.8%) of the title compound. An analytical sample was prepared by recrystallization from isopropyl alcohol.

Workup

  1. customequipped with a mechanical stirrer, a nitrogen inlet and a constant addition funnel
  2. stirringstirred at room temperature overnight
  3. filtrationfiltered
  4. washwashed with ethyl ether
  5. customThe material thus obtained
  6. filtrationThe solid was filtered
  7. washwashed well with H2O
  8. customdried in vacuo

Sources & evidence

ORD record
ord-b2b82acdbf4441b98edc7bb6d8fa0067
Source dataset
uspto-grants-1995_11
Patent number
US05470853

Reaction notes

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