Bromine → HCID 14520027, compound

HRID 2072903Notes

Reaction equation

HRID 2072903 reaction equation
[Br:1]Br.[CH3:3][O:4][C:5](=[O:25])[CH2:6][N:7]([C:9]([C:11]1[C:20]2[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=2)[CH:14]=[CH:13][C:12]=1[O:23][CH3:24])=[O:10])[CH3:8].OS([O-])=O.[Na+]>C(O)(=O)C.O>[CH3:3][O:4][C:5](=[O:25])[CH2:6][N:7]([C:9]([C:11]1[C:20]2[C:15](=[C:16]([Br:1])[C:17]([O:21][CH3:22])=[CH:18][CH:19]=2)[CH:14]=[CH:13][C:12]=1[O:23][CH3:24])=[O:10])[CH3:8]

Participants

6

Reactant 3

HCID 24408BromineHCID 14520026HCID 14520026, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 14520027HCID 14520027, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

A solution of bromine (1.75 mL, 34.05 mmol) in acetic acid (40 mL) was added over 25 minutes to a stirred solution of N-[(2,6-dimethoxy-1-naphthalenyl)carbonyl]-N-methylglycine methyl ester (10.70 g, 33.72 mmol, described in Example 2) in acetic acid (120 mL). After an additional 10 minutes the reaction was diluted with water (900 mL) and NaHSO3 (2.0 g) was added. The resulting precipitate was collected by filtration, washed with water and dried to give 8.93 g (67% yield) of the title compound, m.p. 142°-144° C.

Workup

  1. additionwas added
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-d3c04005da5d41ee8fc82da6860871ab
Source dataset
uspto-grants-1990_04
Patent number
US04914243

Reaction notes

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