Nitric Acid → HCID 22116147, compound

HRID 1276340Notes

Reaction equation

HRID 1276340 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:3]=1.[N+:17]([O-])([OH:19])=[O:18].C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[C:5]([OH:8])=[C:6]([N+:17]([O-:19])=[O:18])[CH:7]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 10340Sodium CarbonateHCID 22116137HCID 22116137, compound

Product 1

HCID 22116147HCID 22116147, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 12.5 g (54.56 mmol) 4-chloro-2-[2-(pyridin-2-yl)ethyl]phenol in 80 ml acetic acid is added portionwise to a nitrating mixture of 70% nitric acid (8.59 g, 136.39 mmol) in 20 ml acetic acid at 5-10° C. The reaction mixture is left to stir at this temperature for 2.5 hours. The pH of the reaction mixture is then adjusted to pH 5.5-6.0 (pH meter) by the addition of a saturated solution of sodium carbonate. The resulting reaction mixture is then extracted with EtOAc (3×300 ml). Concentration of the organic extracts in vacuo yielded a brown oil. This oil is purified by flash chromatography (SiO2, 30% EtOAc in hexane) to give the title compound as a yellow solid, (12.48 g, 82%), m.p. 97-100° C. δH (250 MHz, CDCl3), 11.1 (bs, 1H), 8.57-8.55 (m, 1H), 7.94 (d, J=2.6 Hz, 1H), 7.60 (dt, J=7.7,1.7 Hz, 1H), 7.35 (d, J=2.5 Hz, 1H), 7.17-7.11 (m, 2H), 3.21-3.08 (m, 4H).

Workup

  1. waitThe reaction mixture is left
  2. customThe resulting reaction mixture
  3. extractionis then extracted with EtOAc (3×300 ml)
  4. customConcentration of the organic extracts in vacuo yielded a brown oil
  5. customThis oil is purified by flash chromatography (SiO2, 30% EtOAc in hexane)

Sources & evidence

ORD record
ord-a96b811533a24524a10dc1883505bcb1
Source dataset
uspto-grants-2000_12
Patent number
US06166041

Reaction notes

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