Acetic Acid → HCID 70204147, compound

HRID 617232Notes

Reaction equation

HRID 617232 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][CH2:13][C:14]([CH3:17])([NH2:16])[CH3:15])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[Cl:18][C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([Cl:27])[CH:26]=1)[CH:22]=O.[BH4-].[Na+].C(O)(=O)C>C(O)C>[ClH:1].[ClH:18].[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][CH2:13][C:14]([CH3:17])([NH:16][CH2:22][C:21]3[CH:20]=[C:19]([Cl:18])[CH:26]=[C:25]([Cl:27])[CH:24]=3)[CH3:15])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 357463,5-DichlorobenzaldehydeHCID 4311764Sodium borohydrideHCID 54478391HCID 54478391, compound

Product 1

HCID 70204147HCID 70204147, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1.25 g of N1 -(7-chloro-quinolin-4-yl)-2-methyl-propane-1,2-diamine and 0.88 g of 3,5-dichlorobenzaldehyde were heated under reflux in 10 ml of ethanol for 3 hours. The solvent was evaporated in a vacuum in order to complete the reaction. The resulting Schiff's base was again taken up in 10 ml of ethanol and reduced to the amine by the addition of 0.19 g of sodium borohydride. Excess reducing agent was decomposed after 3 hours by the addition of 10 ml of glacial acetic acid. The turbid solution was then evaporated on a rotary evaporator. The residue was taken up in 10 ml of methanol, which was again evaporated. Addition of methanol and evaporation were repeated twice. The evaporation residue was then dissolved in 15 ml of hot methanol. After the addition of 3.6 ml of 3N isopropanolic hydrochloric acid the hydrochloride of the product crystallized upon cooling. The crude salt (1.1 g) was purified by recrystallization from 30 ml of methanol. Yield: 0.63 g (26%), m.p. >250° C.; 1H-NMR in DMSO-d6, δ (ppm): 1.50 (s, 6H), 4.03 (br.s, 2H), 4.35 (m, 2H), 7.27 (d, J=7 Hz, 1H), 7.69 (m, 1H), 7.82 (dd, J=2 Hz and 9 Hz), 7.89 (m, 2H), 8.11 (d, J=2 Hz, 1H), 8.68 (d, J=7 Hz, 1H), 8.99 (d, J=9 Hz, 1H), 9.65 (br., 1H), 9.8 (m, 2H), 14.5 (br.s, 1H).

Workup

  1. customThe solvent was evaporated in a vacuum in order
  2. customthe reaction
  3. customThe turbid solution was then evaporated on a rotary evaporator
  4. customwhich was again evaporated
  5. additionAddition of methanol and evaporation
  6. dissolutionThe evaporation residue was then dissolved in 15 ml of hot methanol
  7. additionAfter the addition of 3.6 ml of 3N isopropanolic hydrochloric acid the hydrochloride of the product
  8. customcrystallized
  9. temperatureupon cooling
  10. customThe crude salt (1.1 g) was purified by recrystallization from 30 ml of methanol

Sources & evidence

ORD record
ord-c7801ecc85ca4dc6b47e5a8b16b5d68c
Source dataset
uspto-grants-1999_09
Patent number
US05948791

Reaction notes

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