Tetrahydrofuran → HCID 89922666, compound

HRID 921841Notes

Reaction equation

HRID 921841 reaction equation
[NH2:1][C:2]1[C:3]([Cl:15])=[CH:4][C:5]([CH2:10][CH2:11][CH2:12][CH:13]=[O:14])=[C:6]([CH:9]=1)[C:7]#[N:8].C1COCC1.[BH4-].[Na+]>CO>[NH2:1][C:2]1[C:3]([Cl:15])=[CH:4][C:5]([CH2:10][CH2:11][CH2:12][CH2:13][OH:14])=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 89922748HCID 89922748, compound

Product 1

HCID 89922666HCID 89922666, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

5-amino-4-chloro-2-(4-oxobutyl)benzonitrile (544 mg, 2.443 mmol) was taken up in MeOH (6 mL) and THF (2.000 mL) and cooled to 0° C. NaBH4 (277 mg, 7.33 mmol) was added, and the reaction was stirred at 0° C. for 2 h (reaction followed by TLC until no SM detected). The reaction was quenched with water and extracted 2× with DCM. The organic layers were combined, dried over Na2SO4, filtered, and concentrated. The material was purified by flash column chromatography (0-50% EtOAc/DCM; 40 g column). 5-amino-4-chloro-2-(4-hydroxybutyl)benzonitrile (260 mg) was obtained as a yellow glass.

Workup

  1. customreaction
  2. customThe reaction was quenched with water
  3. extractionextracted 2× with DCM
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe material was purified by flash column chromatography (0-50% EtOAc/DCM; 40 g column)

Sources & evidence

ORD record
ord-0d58762ca04448f4b1f85c33137e5597
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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