Benzene → HCID 12640216, compound

HRID 1680449Notes

Reaction equation

HRID 1680449 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][N:6]=1)=[O:4].[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O.C1C=CC=CC=1>O>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]=[CH:16][C:15]2[CH:18]=[CH:19][CH:20]=[C:13]([Cl:12])[CH:14]=2)=[CH:7][N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 241BenzeneHCID 114773-ChlorobenzaldehydeHCID 12457877Methyl 5-aminopyridine-2-carboxylate

Product 1

HCID 12640216HCID 12640216, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The starting material is prepared as follows: the mixture of 30.44 g of 5-aminopyridine-2-carboxylic acid methyl ester, 30.9 g of m-chlorobenzaldehyde, and 400 ml of benzene is refluxed for 3 days on a water-separating trap. The initial suspension eventually becomes a pale yellow solution, which is evaporated. The residual yellow solid is recrystallized from benzene-ethyl acetate-diethyl ether, to yield the 5-(m-chlorobenzylideneamino)-pyridine-2-carboxylic acid methyl ester melting at 139°-142°.

Workup

  1. customThe starting material is prepared
  2. customseparating trap
  3. customis evaporated
  4. customThe residual yellow solid is recrystallized from benzene-ethyl acetate-diethyl ether

Sources & evidence

ORD record
ord-8bcc0ee4fbdc4441a9a9e3dd765e054d
Source dataset
uspto-grants-1981_06
Patent number
US04273779

Reaction notes

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