Hydrochloric Acid → 7-(3-[4-Acetyl-3-hydroxy-2-n-propylphenoxy]-2-hydroxypropoxy)-4-hydroxy-3-nitrocoumarin

HRID 1706461Notes

Reaction equation

HRID 1706461 reaction equation
[N+:1]([O-:4])(O)=[O:2].[C:5]([C:8]1[CH:31]=[CH:30][C:11]([O:12][CH2:13][CH:14]([OH:29])[CH2:15][O:16][C:17]2[CH:26]=[C:25]3[C:20]([C:21]([OH:28])=[CH:22][C:23](=[O:27])[O:24]3)=[CH:19][CH:18]=2)=[C:10]([CH2:32][CH2:33][CH3:34])[C:9]=1[OH:35])(=[O:7])[CH3:6].Cl>C(Cl)(Cl)Cl>[C:5]([C:8]1[CH:31]=[CH:30][C:11]([O:12][CH2:13][CH:14]([OH:29])[CH2:15][O:16][C:17]2[CH:26]=[C:25]3[C:20]([C:21]([OH:28])=[C:22]([N+:1]([O-:4])=[O:2])[C:23](=[O:27])[O:24]3)=[CH:19][CH:18]=2)=[C:10]([CH2:32][CH2:33][CH3:34])[C:9]=1[OH:35])(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 944Nitric AcidHCID 546860317-(3-[4-Acetyl-3-hydroxy-2-n-propylphenoxy]-2-hydroxypropoxy)-4-hydroxycoumarin

Product 1

HCID 546860227-(3-[4-Acetyl-3-hydroxy-2-n-propylphenoxy]-2-hydroxypropoxy)-4-hydroxy-3-nitrocoumarinYield 78%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Fuming nitric acid (9 ml) was added to a stirred suspension of 7-(3-[4-Acetyl-3-hydroxy-2-n-propylphenoxy]-2-hydroxypropoxy)-4-hydroxycoumarin (2.8 g) in chloroform (300 ml) over 1 hr at 0° and the dark mixture stirred for a further 0.5 hr at this temperature. Dilute hydrochloric acid (150 ml) was added and the chloroform removed in vacuo at 0°. The solid which separated was removed by filtration and recrystallised from ethanol to give 2.42 g, (78%) of yellow solid of mp 201°-203° (dec). νmax (mull) 3350 (br), 1770, 1620, 1610, 1540 cm-1 ; τ(DMSO); 9.17 (3H, t, J 6.9 Hz); 8.55 (2H, m, J ca 7 Hz); 7.43 (3H, S+2H, m); 5.78 (5H, S); 3.20 (3H, m); 2.16 (2H, exchangeable S); 2.16 (2H, near doublet); 1 low field broad exchangeable). (Found; C, 58.49; H, 5.07; N, 3.04; C23H23NO10 requires; C, 58.35; H, 4.90; N, 2.96%).

Workup

  1. customthe chloroform removed in vacuo at 0°
  2. customThe solid which separated
  3. customwas removed by filtration
  4. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-97bc889393624723ab2b2109d436eb3d
Source dataset
uspto-grants-1980_06
Patent number
US04207335

Reaction notes

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