Hydrazine hydrate (1:1) → HCID 178518771, compound

HRID 521403Notes

Reaction equation

HRID 521403 reaction equation
O=[C:2]1[C:15]2[C:14]([C:16]([O:18]C)=O)=[CH:13][CH:12]=[CH:11][C:10]=2[NH:9][C:8]2[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=2.O.[NH2:21][NH2:22]>CC(N(C)C)=O>[N:21]1[NH:22][C:16](=[O:18])[C:14]2[CH:13]=[CH:12][CH:11]=[C:10]3[C:15]=2[C:2]=1[C:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C:8]=1[NH:9]3

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 89656024HCID 89656024, compound

Product 1

HCID 178518771HCID 178518771, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
130 °C

Procedure

To the solution of the crude methyl 9-oxo-5,6,7,8,9,10-hexahydroacridine-1-carboxylate in DMA (4 mL) was added hydrazine hydrate (4 mL) at room temperature, and the mixture was heated at 130° C. for 4.0 h. The reaction mixture was cooled to room temperature and stirred for another 12 hours. Then the mixture was filtered and recrystallized from MeOH (twice) to give the product (20 m g, 15%) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThen the mixture was filtered
  3. customrecrystallized from MeOH (twice)
  4. customto give the product (20 m g, 15%) as a yellow solid

Sources & evidence

ORD record
ord-15d0f30cbf22437ab90bb0858c9ac8d2
Source dataset
uspto-grants-2016_05
Patent number
US09328111B2

Reaction notes

Loading…