Formaldehyde → HCID 20074934, compound

HRID 1709730Notes

Reaction equation

HRID 1709730 reaction equation
[C:1]([C:4]1[C:14]2=[C:15]3[C:10](=[CH:11][CH:12]=[CH:13]2)[CH2:9][CH2:8][CH2:7][N:6]3[N:5]=1)(=[O:3])[CH3:2].[CH2:16]=O.[Cl-:18].[CH3:19][NH2+:20][CH3:21]>C(O)(=O)C>[ClH:18].[N:5]1[N:6]2[C:15]3[C:10]([CH2:9][CH2:8][CH2:7]2)=[CH:11][CH:12]=[CH:13][C:14]=3[C:4]=1[C:1](=[O:3])[CH2:2][CH2:19][N:20]([CH3:16])[CH3:21]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 12954980Dimethylazanium;chlorideHCID 20074920HCID 20074920, compound

Product 1

HCID 20074934HCID 20074934, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.5 g (7.5 mmol) of 2-acetyl-7,8-dihydro-6H-pyrazolo[4,5,1-ij]quinoline together with 0.45 g (15 mmol) of paraformaldehyde and 1.35 g (16 mmol) of dimethylammonium chloride in 50 ml of acetic acid was stirred for 2 hours at 100° C. The mixture was evaporated in vacuum, and the residue was shaken with a mixture of methylene chloride and sodium hydroxide solution. The organic layer was washed with saline and evaporated in vacuum. The residue was chromatographed over silicagel using methylene chloride/methanol/ammonia (92.5/7/0.5) as an eluent. The desired fractions were evaporated in vacuum, and the residue was dissolved in alcoholic hydrochloric acid. 0.76 g (35%) of 1-(7,8-dihydro-6H-pyrazolo[4,5,1-ij]quinoline-2-yl)-3-(N,N-dimethylamino)-propan-1-one hydrochloride were obtained after evaporating in vacuum. This product (0.76 g, 2.6 mmol) was boiled for 18 hours together with 1 g (12 mmol) of 2-methyl-imidazole in a mixture of 20 ml of water and 5 ml of propanol-1. The mixture was diluted with 2N sodium hydroxide and extracted with methylene chloride. The organic layer was separated and evaporated in vacuum. The residue was chromatographed over silicagel using methylene chloride/methanol/ammonia (92.5/7/0.5) as an eluent. 0.5 g (69%) of the desired product were obtained; melting point 133°-134° C. 13C NMR (CDCl3, Ref.: TMS):

Workup

  1. customThe mixture was evaporated in vacuum
  2. washThe organic layer was washed with saline
  3. customevaporated in vacuum
  4. customThe residue was chromatographed
  5. customThe desired fractions were evaporated in vacuum
  6. dissolutionthe residue was dissolved in alcoholic hydrochloric acid

Sources & evidence

ORD record
ord-57e7ddff41d54a1e845673dac435c948
Source dataset
uspto-grants-1990_08
Patent number
US04950759

Reaction notes

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