Ethyl Acetate → 6-Methoxycarbonylmethoxy-8-(3-nitrophenyl)-1,7-naphthyridine

HRID 369027Notes

Reaction equation

HRID 369027 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=3)[N:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.C(=O)([O-])[O-].[K+].[K+].[CH3:27][O:28][C:29](=[O:32])[CH2:30]Br.C(OCC)(=O)C>CC(C)=O.CN(C)C=O>[CH3:27][O:28][C:29]([CH2:30][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=3)[N:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2)=[O:32]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 1785266086-Hydroxy-8-(3-nitrophenyl)-1,7-naphthyridine

Product 1

HCID 232846436-Methoxycarbonylmethoxy-8-(3-nitrophenyl)-1,7-naphthyridine

Reagents, catalysts & solvents 1

HCID 18184436N,N-dimethylformamide acetoneSolvent

Procedure

A suspension of 6-hydroxy-8-(3-nitrophenyl)-1,7-naphthyridine (107 mg, 0.40 mmol; produced according to the preceeding example, optionally without further purification), potassium carbonate (55 mg, 0.40 mmol) and bromoacetic acid methyl ester (37 μl, 0.4 mmol) is stirred for two hours in acetone-dimethylformamide (2 ml, 1:1) at ambient temperature. Ethyl acetate is added and the organic phase is washed with 2N NaOH. the solvent is removed in vacuo and the crude product is purified by preparative thin-layer chromatography to give the title compound. Mass M+H 340; mp 160-162° C.

Workup

  1. customproduced
  2. washthe organic phase is washed with 2N NaOH
  3. customthe solvent is removed in vacuo
  4. customthe crude product is purified by preparative thin-layer chromatography

Sources & evidence

ORD record
ord-318accdb996a4bdaa964a136a6312c52
Source dataset
uspto-grants-2000_10
Patent number
US06136821

Reaction notes

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