Sodium Bicarbonate → HCID 18617490, compound

HRID 1264234Notes

Reaction equation

HRID 1264234 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)[CH:6]=[CH:5][N:4]=1)#[N:2].C(=O)(O)[O-:20].[Na+]>S(=O)(=O)(O)O>[C:1]([C:3]1[CH:8]=[C:7]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)[CH:6]=[CH:5][N:4]=1)(=[O:20])[NH2:2]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 18617819HCID 18617819, compound

Product 1

HCID 18617490HCID 18617490, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of methyl 4-(2-cyano-pyridin-4-yl)-benzoate (400 mg, 1.68 mmol) (reference example 57) in 80% sulphuric acid (3 mL) is stirred at room temperature for 12 hours. The resulting solution is poured onto ice and the mixture brought to pH 8 with sat. sodium bicarbonate solution then extracted with ethyl acetate, washed with brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (eluting with 40% ethyl acetate in chloroform) to give 340 mg of the title compound. 1H NMR (CDCl3) δ 3.94 (s, 3H), 5.72 (bs, 1H), 7.67 (dd, J=5, 1 Hz, 1H), 7.75 (d, J=8 Hz, 2H), 7.9 (bs, 1H), 8.15 (d, J=8 Hz, 2H), 8.46 (bs, 1H), 8.63 (d, J=5 Hz, 1H). MS (EI) m/z 256.

Workup

  1. additionThe resulting solution is poured onto ice
  2. extractionthen extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue is purified by flash chromatography (eluting with 40% ethyl acetate in chloroform)

Sources & evidence

ORD record
ord-28af09f7876244f0a8281fbad69494be
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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