3-Cyclopentyloxy-4-methoxybenzaldehyde → HCID 178490958, compound

HRID 582128Notes

Reaction equation

HRID 582128 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][NH:4][N:3]=1.[CH:7]1([O:12][C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=2[O:21][CH3:22])[CH:16]=O)[CH2:11][CH2:10][CH2:9][CH2:8]1.C([BH3-])#N.[Na+]>CO.Cl>[CH:7]1([O:12][C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=2[O:21][CH3:22])[CH2:16][NH:1][C:2]2[CH:6]=[CH:5][NH:4][N:3]=2)[CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

6

Reactant 3

HCID 27358933-Cyclopentyloxy-4-methoxybenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 178418806HCID 178418806, compound

Product 1

HCID 178490958HCID 178490958, compoundYield 30.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 887MethanolSolvent

Procedure

To a solution of 3-aminopyrazole (1.5 g, 0.018 mol) in 50 ml of methanol and 7.5 ml of 1N aqueous HCl was added 3-cyclopentyloxy-4-methoxybenzaldehyde (3.3 g, 0.015 mol) and 95% sodium cyanoborohydride (1.0 g, 0.015 mol). The solution was stirred at room temperature for 20 hours after which concentrated aqueous hydrochloric acid (Hcl) was added to pH 2. The solvent was evaporated at reduced pressure and the residue was extracted twice with 50 ml portions of ether. The ether extracts were discarded and the aqueous solution was brought to pH 10 with 5N aqueous NaOH. The mixture was extracted twice with 50 ml portions of ethyl acetate. The combined ethyl acetate extracts were dried (MgSO4) and evaporated. The solid residue was triturated with ether to give the pure title compound (1.3 g, 30%), mp 106-110° C.

Workup

  1. additionwas added to pH 2
  2. customThe solvent was evaporated at reduced pressure
  3. extractionthe residue was extracted twice with 50 ml portions of ether
  4. extractionThe mixture was extracted twice with 50 ml portions of ethyl acetate
  5. dry with materialThe combined ethyl acetate extracts were dried (MgSO4)
  6. customevaporated
  7. customThe solid residue was triturated with ether

Sources & evidence

ORD record
ord-4c884ff17c514d13821902ba7071986f
Source dataset
uspto-grants-1999_07
Patent number
US05922751

Reaction notes

Loading…