Hydrazine → HCID 67165184, compound

HRID 12212Notes

Reaction equation

HRID 12212 reaction equation
C([N:9]1[CH2:21][C:20](=O)[C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([Cl:23])[CH:17]=3)[NH:12][C:11]=2[CH2:10]1)(=O)C1C=CC=CC=1.[NH2:24]N>>[NH2:24][C:20]1[C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([Cl:23])[CH:17]=3)[NH:12][C:11]=2[CH:10]=[N:9][CH:21]=1

Participants

3

Reactant 2

HCID 9321HydrazineHCID 67163785HCID 67163785, compound

Product 1

HCID 67165184HCID 67165184, compoundYield 30%

Conditions

Temperature
130 °C

Procedure

Crude 2-benzoyl-6-chloro-1,2,3,9-tetrahydro-β-carbolin-4-one (4 g) was dissolved in 30 ml of anhydrous hydrazine and stirred at reflux (130° C. oil bath) under N2 for 6 hours, after which the reaction mixture was allowed to cool to room temperature and sit overnight. The precipitated yellow solids were removed by filtration and washed with water, 2×5 ml, to yield 785 mg (30%) of 4-amino-6-chloro β-carboline as an off white solid. Additional water was added to the combined filtrates until no further precipitation occurred. These solids were also removed by filtration to give 1.056 g (39%) of 4-amino-6-chloro β-carboline as yellow solids, (69% total yield).

Workup

  1. temperatureto cool to room temperature
  2. customThe precipitated yellow solids were removed by filtration
  3. washwashed with water, 2×5 ml

Sources & evidence

ORD record
ord-7898338d32e44508a9b26d36d2f6cd9f
Source dataset
uspto-grants-2010_06
Patent number
US07727985B2

Reaction notes

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