Hydrochloric Acid → HCID 18701920, compound

HRID 342782Notes

Reaction equation

HRID 342782 reaction equation
[O-2].[Mg+2].[Br:3][CH2:4][CH2:5][CH2:6]Br.[Cl:8][C:9]1[CH:10]=[C:11]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:12]=[CH:13][C:14]=1[NH2:15].Cl>CC(N(C)C)=O>[Cl:8][C:9]1[CH:10]=[C:11]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:12]=[CH:13][C:14]=1[NH:15][CH2:6][CH2:5][CH2:4][Br:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 80011,3-DibromopropaneHCID 6850729Magnesium monoxideHCID 13616273Methyl 2-(4-amino-3-chlorophenyl)acetate

Product 1

HCID 18701920HCID 18701920, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Conditions

Temperature
80 °C

Procedure

Magnesium oxide (10 grams, 250 mmoles), was added to a solution of 1,3-dibromopropane (139 grams, 70 mL, 700 mmoles) in dimethylacetamide (150 mL). A solution of methyl 3-chloro-4-aminophenylacetate.HCl (23.6 grams, 100 mmoles) in dimethylacetamide (200 mL) was added dropwise over 30 minutes and the mixture stirred at 80° C. for 6 hours. The cooled mixture was partitioned with methylene chloride and water. The aqueous phase was extracted with methylene choride and the combined organic phases washed with brine, dried over magnesium sulfate and concentrated in vacuo to an oil. The crude product was chromatographed on a silica gel column eluting with hexane:ethyl acetate (9:1). The product was further purified by a second silica gel chromatography in methylene chloride:hexane (2:3) to give the title compound as an oil. NMR, (CDCl3): δ2.15 (qnt, 2H); 3.35 (q, 2H); 3.47 (s,2H); 3.49 (t, 2H); 3.67 (s, 3H); 6.63 (d, 1H); 7.03 (dd, 1H); 7.17 (d, 1H).

Workup

  1. customThe cooled mixture was partitioned with methylene chloride and water
  2. extractionThe aqueous phase was extracted with methylene choride
  3. washthe combined organic phases washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo to an oil
  6. customThe crude product was chromatographed on a silica gel column
  7. washeluting with hexane:ethyl acetate (9:1)
  8. customThe product was further purified by a second silica gel chromatography in methylene chloride:hexane (2:3)

Sources & evidence

ORD record
ord-1f1f8bc821be4eb1917fbbb668b4e6bf
Source dataset
uspto-grants-1999_01
Patent number
US05859051

Reaction notes

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