4-Chlorobutyryl chloride → HCID 86666791, compound

HRID 510860Notes

Reaction equation

HRID 510860 reaction equation
[NH2:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8].Cl[CH2:16][CH2:17][CH2:18][C:19](Cl)=[O:20].CC(C)([O-])C.[K+]>CN(C)C1C=CN=CC=1.O1CCCC1>[C:10]([C:4]1[C:3]([O:13][CH3:14])=[C:2]([N:1]2[CH2:16][CH2:17][CH2:18][C:19]2=[O:20])[C:7]([CH3:8])=[C:6]([Cl:9])[CH:5]=1)(=[O:12])[CH3:11]

Participants

6

Reactant 3

HCID 783704-Chlorobutyryl chlorideHCID 23665647Potassium tert-butoxideHCID 86666790HCID 86666790, compound

Product 1

HCID 86666791HCID 86666791, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 1-(3-amino-5-chloro-2-methoxy-4-methylphenyl)ethanone (100 mg, 0.5 mmol) and 4-dimethylaminopyridine (69 mg, 0.56 mmol) in tetrahydrofuran (1 mL) was added 4-chlorobutanoyl chloride (0.058 mL, 0.52 mmol). The reaction was stirred at room temperature for 1 hour. To the reaction mixture was added 1.0 M potassium tert-butoxide in tetrahydrofuran (1.03 mL, 1.03 mmol). The resulting mixture was stirred at room temperature for 2 hours, quenched with aq. ammonium chloride and extracted with ethyl acetate. The combined organic layers were washed with water, brine, dried and evaporated. The residue was purified on silica gel, eluting with 0 to 50% ethyl acetate in hexane, to give the product (20 mg, 20%). LCMS calculated for C14H17ClNO3 (M+H)+: m/z=282.1. found: 282.1.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 2 hours
  2. customquenched with aq. ammonium chloride
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with water, brine
  5. customdried
  6. customevaporated
  7. customThe residue was purified on silica gel
  8. washeluting with 0 to 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-0898ca3b972146a0bbf48ee3478dc316
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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