Hydrazine hydrate (1:1) → HCID 178422982, compound

HRID 521407Notes

Reaction equation

HRID 521407 reaction equation
O[C:2]1[C:3]2[CH2:4][C:5](C)(C)[CH2:6][CH2:7][C:8]=2[N:9]=[C:10]2[C:15]=1[C:14]([C:16](OC)=O)=[CH:13][CH:12]=[CH:11]2.[OH2:22].[NH2:23][NH2:24].[CH3:25]C(N(C)C)=O>>[CH3:25][C:11]1[CH:12]=[CH:13][C:14]2[C:16](=[O:22])[NH:23][N:24]=[C:2]3[C:15]=2[C:10]=1[NH:9][C:8]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]=13

Participants

4

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 31374DimethylacetamideHCID 178497568HCID 178497568, compound

Product 1

HCID 178422982HCID 178422982, compound

Procedure

A solution of methyl 9-hydroxy-7,7-dimethyl-5,6,7,8-tetrahydroacridine-1-carboxylate (0.18 g, 0.63 mmol) and hydrazine hydrate (2.5 mL) in DMA (4 mL) was heated at 130° C. for 4 hours. The reaction mixture was cooled to room temperature, the resulting precipitate was collected by filtration, washed with MeOH (cold, 5 mL) and water (30 mL). Then the precipitate was recrystalized with MeOH to afford a yellow solid (95 mg). 1H NMR (DMSO-d6) δ 11.6 (s, 1H), 9.05 (s, 1H), 7.46 (d, 1H, J=7.8 Hz), 7.38 (d, 1H, J=7.8 Hz), 2.52-2.54 (m, 2H), 2.34 (s, 3H), 2.24-2.26 (m, 2H), 1.68-1.72 (m 4H). MS (ESI) m/e [M+1]+254.0.

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. washwashed with MeOH (cold, 5 mL) and water (30 mL)
  3. customThen the precipitate was recrystalized with MeOH

Sources & evidence

ORD record
ord-a82f74195b8b4809b3b6273958adcb6c
Source dataset
uspto-grants-2016_05
Patent number
US09328111B2

Reaction notes

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