3-Cyclopentyloxy-4-methoxybenzaldehyde → HCID 178491044, compound

HRID 582130Notes

Reaction equation

HRID 582130 reaction equation
[NH2:1][C:2]1[C:6]([C:7]([OH:9])=[O:8])=[CH:5][NH:4][N:3]=1.[CH:10]1([O:15][C:16]2[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=2[O:24][CH3:25])[CH:19]=O)[CH2:14][CH2:13][CH2:12][CH2:11]1.C([BH3-])#N.[Na+]>CO>[CH:10]1([O:15][C:16]2[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=2[O:24][CH3:25])[CH2:19][NH:1][C:2]2[C:6]([C:7]([OH:9])=[O:8])=[CH:5][NH:4][N:3]=2)[CH2:11][CH2:12][CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 27358933-Cyclopentyloxy-4-methoxybenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 178509273HCID 178509273, compound

Product 1

HCID 178491044HCID 178491044, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 3-aminopyrazole-4-carboxylic acid (3.56 g, 0.023 mol) in 400 ml of methanol was added 3-cyclopentyloxy-4-methoxybenzaldehyde (5.06 g, 0.023 mole) and 95% sodium cyanoborohydride (1.85 g, 0.028 mol). The reaction mixture was stirred for 16 hours and then the methanol was evaporated under reduced pressure. The residue was treated with 100 ml of 15% aqueous NaOH and extracted twice with 100 ml portions of ether. The aqueous layer was acidified to pH 5 with 5N aqueous HCl and extracted twice with 100 ml portions of ethyl acetate. The ethyl acetate extracts were evaporated under reduced pressure and the residue was triturated with ether to give 3.7 g (49%) of the title compound, mp 134-136°, after recrystallization from methanol.

Workup

  1. customthe methanol was evaporated under reduced pressure
  2. additionThe residue was treated with 100 ml of 15% aqueous NaOH
  3. extractionextracted twice with 100 ml portions of ether
  4. extractionextracted twice with 100 ml portions of ethyl acetate
  5. customThe ethyl acetate extracts were evaporated under reduced pressure
  6. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-79ab203ca4b641d487ace948b8e80f72
Source dataset
uspto-grants-1999_07
Patent number
US05922751

Reaction notes

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