N-bromobutanimide → HCID 22397020, compound

HRID 1070453Notes

Reaction equation

HRID 1070453 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([OH:16])=[CH:8][C:7]=1[OH:17])=[O:5])[CH3:2].C1C(=O)N([Br:25])C(=O)C1>C(#N)C>[CH2:1]([O:3][C:4]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([OH:16])=[C:8]([Br:25])[C:7]=1[OH:17])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 12249847HCID 12249847, compound

Product 1

HCID 22397020HCID 22397020, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of ethyl-2,4-dihydroxy-1-naphthoate [Bruggink and McKillop Tetrahedron 31, 2607, 1975] (0.1 g, 0.43 mmol) in acetonitrile (2 mL) was added NBS (84 mg, 0.47 mmol). The mixture was stirred at RT for 30 min. The acetonitrile was removed in vacuo and CCl4 was added. The solution was filtered and concentrated. The crude product was purified by chromatography (eluting with DCM) to give the product (0.13 g, 93% yield) as a white solid. 1H NMR (CDCl3) δ 13.61 (s, 1H), 8.79 (d, 1H), 8.24 (d, 1H), 7.58 (t, 1H), 7.41 (t, 1H), 6.61 (s, 1H), 4.60 (q, 2H), 1.55 (t. 3H). MS APCI negative mode m/z 310.84.

Workup

  1. customThe acetonitrile was removed in vacuo and CCl4
  2. additionwas added
  3. filtrationThe solution was filtered
  4. concentrationconcentrated
  5. customThe crude product was purified by chromatography (eluting with DCM)

Sources & evidence

ORD record
ord-97564b4fd60846278bd7d6750e769283
Source dataset
uspto-grants-2005_06
Patent number
US06903092B2

Reaction notes

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