Nitric Acid → HCID 13216231, compound

HRID 27720Notes

Reaction equation

HRID 27720 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([NH:10][C:11]([CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[O:12])[CH:3]=1.[N+:19]([O-])([OH:21])=[O:20].[OH-].[Na+]>C(O)(=O)C.S(=O)(=O)(O)O>[Cl:1][C:2]1[C:7]([N+:19]([O-:21])=[O:20])=[CH:6][C:5]([O:8][CH3:9])=[C:4]([NH:10][C:11]([CH:13]2[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]2)=[O:12])[CH:3]=1

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 13216230HCID 13216230, compound

Product 1

HCID 13216231HCID 13216231, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Procedure

4-Chloro-2-(piperidine-4-carboxamido)anisole (10.4 g) was dissolved in a mixture of acetic acid (100 ml) and concentrated sulphuric acid (5 ml). Fuming nitric acid (2.1 ml) was added dropwise, keeping the temperature below 30°. The solution was stirred at room temperature for 2 hr, poured onto crushed ice (ca 500 ml) and basified with 40% sodium hydroxide. The mixture was extracted with ethyl acetate (2×250 ml), the extracts dried (K2CO3) and solvent removed at the pump. The brown residue was crystallised from ethyl acetate and petroleum ether (b.p. 60°-80°), giving 4-chloro-5-nitro-2-(piperidine-4-carboxamido)anisole as brown plates (e17) (9.9 g, 82%), m.p. 167°-170°.

Workup

  1. customthe temperature below 30°
  2. additionpoured
  3. extractionThe mixture was extracted with ethyl acetate (2×250 ml)
  4. dry with materialthe extracts dried (K2CO3) and solvent
  5. customremoved at the pump
  6. customThe brown residue was crystallised from ethyl acetate and petroleum ether (b.p. 60°-80°)

Sources & evidence

ORD record
ord-c420d9bcea1e46b69e473269556aaf52
Source dataset
uspto-grants-1980_09
Patent number
US04223034

Reaction notes

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