N-bromobutanimide → HCID 117604294, compound

HRID 64510Notes

Reaction equation

HRID 64510 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([NH2:13])[CH:7]=[CH:6]2.[Br:14]N1C(=O)CCC1=O>CC#N>[Br:14][C:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2)[CH:6]=[CH:7][C:8]=1[NH2:13]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 124051106-Methoxynaphthalen-2-amine

Product 1

HCID 117604294HCID 117604294, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

6-Methoxy-2-naphthylamine (400 mg, 1.6 mmol) was suspended in 20 mL of MeCN with 12 mg of NH4OAc (0.16 mmol) and stirred in an ice bath. N-Bromosuccinimide (299 mg, 1.68 mmol) was dissolved in 6 mL of dry MeCN and added slowly over 1 hour (h). The reaction was stirred for an additional hour at 0° C., then adsorbed onto Celite, concentrated under reduced pressure and subjected to silica gel chromatography eluting with 0→60% EtOAc in heptanes to yield 300 mg of an orange solid. 7.94 (d, 1H); 7.55 (d, 1H); 7.18 (dd, 1H); 7.09 (d, 1H); 7.02 (d, 1H); 4.29 (br s, 2H); 3.89 (s, 3H).

Workup

  1. additionadded slowly over 1 hour (h)
  2. stirringThe reaction was stirred for an additional hour at 0° C.
  3. concentrationconcentrated under reduced pressure
  4. washeluting with 0→60% EtOAc in heptanes

Sources & evidence

ORD record
ord-b7212b0ccfcb4338bcb0df1348dd655b
Source dataset
uspto-grants-2016_09
Patent number
US09447450B2

Reaction notes

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