HCID 58529482, compound → HCID 178419325, compound

HRID 1972754Notes

Reaction equation

HRID 1972754 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[NH:9][C:10](=O)[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>Cl.CO>[CH2:11]([C:10]1[NH:1][C:2]2[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=2[N:9]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 1

HCID 58529482HCID 58529482, compound

Product 1

HCID 178419325HCID 178419325, compoundYield 82.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

Concentrated hydrochloric acid (12 drops) was added to a solution of N-(2-amino-5-bromophenyl)-2-phenylacetamide (4.10 g, 13.44 mmol) in methanol (80 mL) and the mixture was stirred at room temperature for 2.5 days. The reaction mixture was concentrated and taken up in DCM. Solid sodium bicarbonate was added in portions to the suspension and the mixture stirred for 30 min. and water (20 mL) was added. The organic layer was isolated and dried over Na2SO4. The product (3.2 g, 82%) was Isolated by purified by column chromatography (50% hexanes in ethyl acetate). LC-MS [M+H]+=288.5, RT=2.11 min

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionSolid sodium bicarbonate was added in portions to the suspension
  3. stirringthe mixture stirred for 30 min.
  4. additionwater (20 mL) was added
  5. customThe organic layer was isolated
  6. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-c97f01824b68426b87ad45b688dadf60
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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