Acetic Acid → HCID 178423614, compound

HRID 521401Notes

Reaction equation

HRID 521401 reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:15][C:14]2[C:13](=O)[C:12]3[C:11]([C:17]([O-])=[O:18])=[CH:10][CH:9]=[CH:8][C:7]=3[NH:6][C:5]=2[CH2:4][CH2:3]1.O.[NH2:22][NH2:23].C(O)(=O)C.C([O-])(O)=O.[Na+]>CC(N(C)C)=O>[CH3:1][C:2]1([CH3:20])[CH2:3][CH2:4][C:5]2[NH:6][C:7]3[C:12]4=[C:11]([C:17](=[O:18])[NH:22][N:23]=[C:13]4[C:14]=2[CH2:15]1)[CH:10]=[CH:9][CH:8]=3

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 516892Sodium BicarbonateHCID 131735500HCID 131735500, compound

Product 1

HCID 178423614HCID 178423614, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
130 °C

Procedure

A solution of 7,7-dimethyl-9-oxo-5,6,7,8,9,10-hexahydroacridine-1-carboxylate (3.3 g, 11.6 mmol) and hydrazine hydrate (15 mL) in DMA (22 mL) was heated at 110° C. for 1.5 h, acetic acid (30 mL) was added and the mixture was stirred at 130° C. for another 4 hours. The reaction mixture was cooled to room temperature, and aqueous NaHCO3 (80 ml) was added to the mixture, filtered. And the filtered cake was washed with water (50 mL) and methanol (30 mL) alternatively multiple times. The solvent was removed in vacuo to give 10,10-Dimethyl-8,9,10,11-tetrahydro-2H-pyridazino[5,4,3-kl]acridin-3(7H)-one as a yellow solid (1.50 g, 49%). 1H NMR (DMSO-d6) δ 11.71 (s, 1H), 10.36 (s, 1H), 7.59-7.63 (m, 1H), 7.42-7.44 (m, 1H), 7.25-7.27 (m, 1H), 2.49-2.52 (m, 2H), 2.10 (s, 2H), 1.55 (m, 2H), and 1.00 (s, 6H). MS (ESI) m/e [M+1]+268.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. washAnd the filtered cake was washed with water (50 mL) and methanol (30 mL) alternatively multiple times
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-fab8fd030f5c45f78b671f20b6b9796c
Source dataset
uspto-grants-2016_05
Patent number
US09328111B2

Reaction notes

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