Formaldehyde → HCID 20244128, compound

HRID 482886Notes

Reaction equation

HRID 482886 reaction equation
C=O.[C:3]([BH3-])#[N:4].[Na+].[ClH:7].N[C:9]1([CH2:12][S:13][C:14]2[C:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)[CH2:11][CH2:10]1.[C:30](=O)(O)[O-].[Na+]>C(O)C.C(O)(=O)C>[ClH:7].[CH3:30][N:4]([CH3:3])[C:9]1([CH2:12][S:13][C:14]2[C:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)[CH2:11][CH2:10]1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 2024412995232-69-2

Product 1

HCID 20244128HCID 20244128, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

Formaldehyde (37% w/w solution in water, 0.82 ml.), glacial acetic acid (0.82 ml.) and sodium cyanoborohydride (0.70 g.) were added to a solution of 2-[(1-aminocyclopropyl)methylthio]-3-phenylquinoline hydrochloride (1.2 g.) in ethanol (35 ml.). The mixture was stirred at ambient temperature for 4 hr., poured into saturated sodium bicarbonate solution (200 ml.), and extracted with ethyl acetate (3×100 ml.). The ethyl acetate extract was washed with brine (3×20 ml.), dried (Na2SO4), and evaporated in vacuo to dryness. The residual oil was chromatographed on silica gel (Merck Kieselgel 60, Art No. 9385, grain size 0.040-0.063 mm., 230-400 mesh ASTM; 180 g.) using chloroform as eluant. The relevant fraction was evaporated in vacuo to dryness, the residual oil (1.1 g.) was dissolved in methanol (20 ml.), and concentrated hydrochloric acid (0.3 ml.) was added. The resulting solution was evaporated in vacuo to dryness, and the residue was crystallised from a mixture of ethanol and diethyl ether, to yield 2-[(1-dimethylaminocyclopropyl)methylthio]-3-phenylquinoline hydrochloride, m.p. 219°.

Workup

  1. extractionextracted with ethyl acetate (3×100 ml.)
  2. extractionThe ethyl acetate extract
  3. washwas washed with brine (3×20 ml.)
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo to dryness
  6. customThe residual oil was chromatographed on silica gel (Merck Kieselgel 60, Art No. 9385, grain size 0.040-0.063 mm., 230-400 mesh ASTM; 180 g.)
  7. customThe relevant fraction was evaporated in vacuo to dryness
  8. dissolutionthe residual oil (1.1 g.) was dissolved in methanol (20 ml.)
  9. additionconcentrated hydrochloric acid (0.3 ml.) was added
  10. customThe resulting solution was evaporated in vacuo to dryness
  11. customthe residue was crystallised from a mixture of ethanol and diethyl ether

Sources & evidence

ORD record
ord-8766f4d07c0741dfbc913e540eab0a33
Source dataset
uspto-grants-1986_03
Patent number
US04576953

Reaction notes

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