Propionic Acid → HCID 18505053, compound

HRID 1437152Notes

Reaction equation

HRID 1437152 reaction equation
S(Cl)([Cl:3])=O.[OH:5][CH2:6][CH2:7][NH:8][C:9]1[C:10]2[C:15]([N:16]=[C:17]3[C:22]=1[C:21]([N+:23]([O-:25])=[O:24])=[CH:20][CH:19]=[C:18]3[CH3:26])=[CH:14][CH:13]=[CH:12][CH:11]=2.[C:27](O)(=[O:30])[CH2:28][CH3:29]>>[ClH:3].[C:27]([O:5][CH2:6][CH2:7][NH:8][C:9]1[C:10]2[C:15]([N:16]=[C:17]3[C:22]=1[C:21]([N+:23]([O-:25])=[O:24])=[CH:20][CH:19]=[C:18]3[CH3:26])=[CH:14][CH:13]=[CH:12][CH:11]=2)(=[O:30])[CH2:28][CH3:29]

Participants

4

Reactant 3

HCID 1032Propionic AcidHCID 24386Thionyl ChlorideHCID 9926215HCID 9926215, compound

Product 1

HCID 18505053HCID 18505053, compoundYield 68%

Procedure

Thionyl chloride (10 ml) is added to a stirred, cooled to −20° C. propionic acid (50 ml) and at the same temperature 9-(2-hydroxyethylamino)-4-methyl-1-nitroacridine (0.55 g) is added in portions, and the mixture is stirred at room temperature for 20 hours. The reaction mixture is distilled off under reduced pressure, washed several times with 10% aqueous sodium bicarbonate and water, dried under vacuum, and crystallized from absolute methanol-ethanol hydrogen chloride solution to give 9-(2-propionoxyethylamino)-4-methyl-1-nitroacridine hydrochloride with 68% yield, m.p. 228-230° C., anal. C19H19N3O4Cl(C,H,N). 1H NMR (d6DMSO): δ 1.20(t, 3H, H-3″), 2.0(q, 2H, H-2″), 2.8(s, 3H, CH3), 3.9(t, 2H, H-1), 4.0(t, 2H, H-2′), 7.4(t, 1H, H-7), 7.5(d, 1H, J=7.8 Hz, H-3), 7.6(d, 1H, J=8.3 Hz, H-6), 8.0(t, 1H, H-5), 8.4(m, 1H, H-8).

Workup

  1. distillationThe reaction mixture is distilled off under reduced pressure
  2. washwashed several times with 10% aqueous sodium bicarbonate and water
  3. customdried under vacuum
  4. customcrystallized from absolute methanol-ethanol hydrogen chloride solution

Sources & evidence

ORD record
ord-4e28a81529144c9a8cbfad924a6f2a19
Source dataset
uspto-grants-2009_11
Patent number
US07622478B2

Reaction notes

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