Sulfuric Acid → 5-(4-Fluorophenyl)pyridine-3-carbaldehyde

HRID 490968Notes

Reaction equation

HRID 490968 reaction equation
N1(C(N)=O)CCOCC1.[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[C:19]([C:23](O)=[O:24])[CH:20]=[N:21][CH:22]=2)=[CH:13][CH:12]=1.S(=O)(=O)(O)O>C1COCC1>[F:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:18]=[C:19]([CH:23]=[O:24])[CH:20]=[N:21][CH:22]=2)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 695290095-(4-Fluorophenyl)pyridine-3-carboxylic acid morpholinamide

Product 1

HCID 98776715-(4-Fluorophenyl)pyridine-3-carbaldehydeYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

6.0 g of 5-(4-fluorophenyl)pyridine-3-carboxylic acid morpholinamide from Example 1(b) are dissolved in 30 ml of THF, and 57 g of a 13.6% LiAlH—(OEt)3 solution in THF are added over the course of 10 minutes at 30° C. to 35° C. After 1 hour, 30 ml of 12.5% sulfuric acid are added, and the organic phase is separated off. The aqueous phase is adjusted to pH 1 using sulfuric acid and extracted a number of times with methyl tert-butyl ether. The organic phases are then combined, extracted once with water and then evaporated, leaving a residue of 4.3 g having a content of 97% by weight of 5-(4-fluorophenyl)pyridine-3-carbaldehyde (yield=98% of theory).

Workup

  1. customthe organic phase is separated off
  2. extractionextracted a number of times with methyl tert-butyl ether
  3. extractionextracted once with water
  4. customevaporated
  5. customleaving a residue of 4.3 g

Sources & evidence

ORD record
ord-a699c572706340d2b27d7bc42d0668d1
Source dataset
uspto-grants-2009_05
Patent number
US07528256B2

Reaction notes

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