3-Nitrobenzaldehyde → HCID 15229832, compound

HRID 2269690Notes

Reaction equation

HRID 2269690 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].COC(OC)OC.[NH2:19][CH2:20][CH2:21][CH2:22][OH:23].[BH4-].[Na+]>CO>[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7][NH:19][CH2:20][CH2:21][CH2:22][OH:23])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 74493-NitrobenzaldehydeHCID 9005Trimethyl orthoformateHCID 90863-Amino-1-propanolHCID 4311764Sodium borohydride

Product 1

HCID 15229832HCID 15229832, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of m-nitrobenzaldehyde (94.23 mmol) and trimethylorthoformate (15.5 mL, 141 mmol) in MeOH (300 mL) is added dropwise 3-amino-1-propanol (7.21 mL, 94.23 mmol) at room temperature. The reaction is allowed to stir at room temperature for 5 hours followed by cooling to 0° C. in an ice bath. Sodium borohydride (3.56 g, 94.23 mmol) is added in two portions and when the bubbling stops the solvent is evaporated. The resulting residue is partitioned between ethyl acetate (75 mL) and water (75 mL). The aqueous layer is extracted twice with ethyl acetate (75 mL). The ethyl acetate extracts are collected and washed twice with Brine (50 mL), dried over MgSO4, filtered, and concentrated. Drying will give the title compound.

Workup

  1. temperatureby cooling to 0° C. in an ice bath
  2. customis evaporated
  3. customThe resulting residue is partitioned between ethyl acetate (75 mL) and water (75 mL)
  4. extractionThe aqueous layer is extracted twice with ethyl acetate (75 mL)
  5. customThe ethyl acetate extracts are collected
  6. washwashed twice with Brine (50 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customDrying will

Sources & evidence

ORD record
ord-2472142dcec74e39854de1511547b75c
Source dataset
uspto-grants-2001_12
Patent number
US06329523B1

Reaction notes

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