Hydrazine hydrate (1:1) → 2-Aminomethyl-8,10,10-trimethyl-10H-pyrido[1,2-a]indolylium perchlorate

HRID 76817Notes

Reaction equation

HRID 76817 reaction equation
[Cl:1]([O-:5])(=[O:4])(=[O:3])=[O:2].O=C1C2C(=CC=CC=2)C(=O)[N:8]1[CH2:17][C:18]1[C+:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[N:23]1[CH2:27][CH:28]=[C:29]([CH3:31])[CH:30]=[C:22]1[C:21]2([CH3:33])[CH3:32].O.NN>C(Cl)Cl.CO>[Cl:1]([O-:5])(=[O:4])(=[O:3])=[O:2].[NH2:8][CH2:17][C:18]1[C+:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[N:23]1[CH2:27][CH:28]=[C:29]([CH3:31])[CH:30]=[C:22]1[C:21]2([CH3:33])[CH3:32]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178427978HCID 178427978, compound

Product 1

HCID 1784279792-Aminomethyl-8,10,10-trimethyl-10H-pyrido[1,2-a]indolylium perchlorate

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

2-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-8,10,10-trimethyl-10H-pyrido[1,2-a]indolylium perchlorate (36 g, 0.077 mol; Sigma-Aldrich) was added to a conical 1-L flask equipped with magnetic stir bar, followed by 480 mL of CH2Cl2—CH3OH mixture (3:2). Stirring was started and hydrazine monohydrate (25 g, 0.50 mol; Aldrich) was added to the reaction mixture at once. Stirring was continued until all solid was dissolved. The flask was closed with a stopper and let to stand at room temperature overnight without stirring. After about 16 hours the precipitated solid phthalhydrazide was filtered off, washed with 100 mL of CH2Cl2—CH3OH mixture (3:2) and discarded. The combined filtrates were evaporated and the resulted solid was washed with Ether-CH3OH. The solid was filtered, washed with ether and dried. The yield was 26 g (100% of theory).

Workup

  1. customequipped with magnetic stir bar
  2. stirringStirring
  3. dissolutionwas dissolved
  4. customThe flask was closed with a stopper
  5. stirringwithout stirring
  6. filtrationAfter about 16 hours the precipitated solid phthalhydrazide was filtered off
  7. washwashed with 100 mL of CH2Cl2—CH3OH mixture (3:2)
  8. customThe combined filtrates were evaporated
  9. washthe resulted solid was washed with Ether-CH3OH
  10. filtrationThe solid was filtered
  11. washwashed with ether
  12. customdried

Sources & evidence

ORD record
ord-7133137f949644b2bc5b70d3ed9c01c6
Source dataset
uspto-grants-2014_09
Patent number
US08835632B2

Reaction notes

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