Sodium Methoxide → HCID 178510520, compound

HRID 1902361Notes

Reaction equation

HRID 1902361 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:3]=1[C:4]([CH:6]([C:11]#[N:12])[C:7](OC)=[O:8])=[O:5].C[O-].[Na+]>N1C=CC=CC=1>[C:11]([C:6]1[C:7]([OH:8])=[N:1][C:2]2[C:3]([C:4]=1[OH:5])=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=2)#[N:12]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 20516620HCID 20516620, compound

Product 1

HCID 178510520HCID 178510520, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A 13.16 g portion of the methyl 2-(2'-amino-5'-nitrobenzoyl)cyanoacetate, produced as described in Example 4 (molecular weight 263) was cyclized by refluxing for 8 hours with 2.81 g sodium methoxide (molecular weight 54) in 60 ml pyridine. After cyclization the pyridine was distilled and the batch was worked up as described above in Example 3. That part of the reaction product which was water insoluble before the acidification was not the desired quinoline derivative and was discarded. The precipitate which formed after acidification of the clear yellowish-brown mother liquor to pH 2.5 was found by infrared spectroscopy and nuclear magnetic resonance to be the crude desired product (melting point 281°-282° C.). The yield was 7.5 g, 64.9 percent of theory based on starting methyl ester of 2-(2'-amino-5'-nitrobenzoyl) cyanoacetate.

Workup

  1. distillationAfter cyclization the pyridine was distilled
  2. customThe precipitate which formed after acidification of the clear yellowish-brown mother liquor to pH 2.5

Sources & evidence

ORD record
ord-2ec2899ef6034c07a57d77e8d126d251
Source dataset
uspto-grants-1982_12
Patent number
US04362876

Reaction notes

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