Nitric Acid → 7-[3-[4-[(4-Chlorophenyl)methyl]-1-piperazinyl]propoxy]-4-hydroxy-3-nitro-2H-1-benzopyran-2-one

HRID 444213Notes

Reaction equation

HRID 444213 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]1[CH:34]=[CH:33][C:9]([CH2:10][N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][O:20][C:21]3[CH:30]=[C:29]4[C:24]([C:25]([OH:32])=[CH:26][C:27](=[O:31])[O:28]4)=[CH:23][CH:22]=3)[CH2:13][CH2:12]2)=[CH:8][CH:7]=1>C(Cl)(Cl)Cl>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:10][N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][O:20][C:21]3[CH:30]=[C:29]4[C:24]([C:25]([OH:32])=[C:26]([N+:1]([O-:4])=[O:2])[C:27](=[O:31])[O:28]4)=[CH:23][CH:22]=3)[CH2:13][CH2:12]2)=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 54710800HCID 54710800, compound

Product 1

HCID 547107967-[3-[4-[(4-Chlorophenyl)methyl]-1-piperazinyl]propoxy]-4-hydroxy-3-nitro-2H-1-benzopyran-2-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Fuming nitric acid (10 ml; d 1.52) was added dropwise over 15 mins to a cold (0° C.) stirred suspension of 1-(4-chlorobenzyl)-4-[3-(4-hydroxycoumarin-7-yloxy)propyl]piperazine (2.0 g) in chloroform (200 ml) and the mixture stirred for a further 1 hour at 0°. The solution which formed precipitated a yellow solid on addition of water which after filtration was washed with ethanol to give 2.62; (95%) of the dinitric acid salt of the title compound of m.p. 142°-144° (dec). νmax (mull) 2700 (br), 1740, 1615, 1525 cm-1. (Found; C, 45.87; H. 4.52; Cl, 5.66; N, 11.36; C23H24ClN3O6 2HNO3 requires; C, 46.05; H, 4.37; Cl, 5.91; N, 11.67%).

Workup

  1. stirringthe mixture stirred for a further 1 hour at 0°
  2. customThe solution which formed
  3. customprecipitated a yellow solid
  4. additionon addition of water which
  5. filtrationafter filtration
  6. washwas washed with ethanol
  7. customto give 2.62

Sources & evidence

ORD record
ord-bafd5ddf67364d4e98e80e3fd88d6328
Source dataset
uspto-grants-1981_04
Patent number
US04263299

Reaction notes

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