Methanol → 2,3-methylenedioxy-11-oxo-11H-pyrido[2,1-b]quinazoline-6-carboxylic acid

HRID 2419015

Reaction equation

HRID 2419015 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[O:12][CH2:13][O:14][C:9]2=[CH:8][C:3]=1[C:4]([O:6]C)=O.Cl[C:16]1[N:24]=[CH:23][CH:22]=[CH:21][C:17]=1[C:18]([OH:20])=[O:19].CO>CN(C=O)C>[CH2:13]1[O:12][C:10]2[CH:11]=[C:2]3[C:3]([C:4](=[O:6])[N:24]4[CH:23]=[CH:22][CH:21]=[C:17]([C:18]([OH:20])=[O:19])[C:16]4=[N:1]3)=[CH:8][C:9]=2[O:14]1

Participants

5

Reactant 3

HCID 887MethanolHCID 762582-Chloronicotinic acidHCID 290838Methyl 6-amino-1,3-benzodioxole-5-carboxylate

Product 1

HCID 203168392,3-methylenedioxy-11-oxo-11H-pyrido[2,1-b]quinazoline-6-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.00g (10.4 mmol) of methyl 2-amino-4,5-methylenedioxybenzoate, 1.67g (10.4 mmol) of 2-chloronicotinic acid and 50mg of KI was heated at 170° for 1 hour. The fusion or melt gradually solidified to an orange cake. The solid material was heated in boiling methanol (250 ml) and then filtered to yield 1.60g of crude product, mp. 273°-280° dec. The analytical sample was obtained by recrystallization from DMF, mp. 300°-304° dec.

Workup

  1. temperaturewas heated at 170° for 1 hour
  2. temperatureThe solid material was heated
  3. filtrationfiltered
  4. customto yield 1.60g of crude product, mp. 273°-280° dec

Sources & evidence

ORD record
ord-6c4ebe5621724a688721fa60eaf7865f
Source dataset
uspto-grants-1978_08
Patent number
US04104389

Linked notes

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