3-Cyclopentyloxy-4-methoxybenzaldehyde → HCID 178490969, compound

HRID 582129Notes

Reaction equation

HRID 582129 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[N:4][CH:3]=1.C([BH3-])#N.[Na+].[CH:11]1([O:16][C:17]2[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=2[O:25][CH3:26])[CH:20]=O)[CH2:15][CH2:14][CH2:13][CH2:12]1>CO.Cl>[CH:11]1([O:16][C:17]2[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=2[O:25][CH3:26])[CH2:20][NH:1][C:2]2[NH:6][N:5]=[N:4][CH:3]=2)[CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

6

Reactant 3

HCID 27358933-Cyclopentyloxy-4-methoxybenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 178508070HCID 178508070, compound

Product 1

HCID 178490969HCID 178490969, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 887MethanolSolvent

Procedure

To a stirred solution of 5-amino-1,2,3-triazole (3.0 g, 0.036 mol) in 100 ml of methanol and 15 ml of 1N HCl was added sodium cyanoborohydride (1.89 g, 0.030 mol) and 3-cyclopentyloxy-4-methoxybenzaldehyde (6.6 g, 0.30 mol). The reaction mixture was stirred at room temperature for 64 hours and then acidified to pH 2 with concentrated HCl. The solution was evaporated at reduced pressure and the residue was treated with water (100 ml) and extracted twice with 100 ml portions of ethyl acetate. The ethyl acetate extracts were combined and extracted twice with 50 ml portions of 3N HCl and then discarded. The aqueous extracts were combined with the original aqueous layer and basified to pH 12 with potassium hydroxide pellets. The alkaline solution was extracted twice with 100 ml portions of ethyl acetate. The ethyl acetate extracts were combined and evaporated to give a solid which was crystallized from ethyl acetate to give 2.9 g (34%) of the title compound mp 113-114° C. collected in two crops.

Workup

  1. customThe solution was evaporated at reduced pressure
  2. additionthe residue was treated with water (100 ml)
  3. extractionextracted twice with 100 ml portions of ethyl acetate
  4. extractionextracted twice with 50 ml portions of 3N HCl
  5. extractionThe alkaline solution was extracted twice with 100 ml portions of ethyl acetate
  6. customevaporated
  7. customto give a solid which
  8. customwas crystallized from ethyl acetate

Sources & evidence

ORD record
ord-e48f2bdc87994c969837173c50551b0c
Source dataset
uspto-grants-1999_07
Patent number
US05922751

Reaction notes

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