1,3-Benzodioxole-5-carboxylic acid → HCID 13579410, compound

HRID 235845Notes

Reaction equation

HRID 235845 reaction equation
[CH2:1]1[O:12][C:11]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=2[O:2]1.[NH2:13][C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[N:17][C:18]([Cl:24])=[CH:19][CH:20]=2)[N:15]=1>O.C(O)CC>[Cl:24][C:18]1[N:17]=[C:16]2[C:21]([CH:22]=[CH:23][C:14]([NH:13][C:6](=[O:8])[C:5]3[CH:9]=[CH:10][C:11]4[O:12][CH2:1][O:2][C:3]=4[CH:4]=3)=[N:15]2)=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 71961,3-Benzodioxole-5-carboxylic acidHCID 851997-Chloro-1,8-naphthyridin-2-amine

Product 1

HCID 13579410HCID 13579410, compoundYield 39.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 10311-PropanolSolvent

Conditions

Temperature
4 °C

Procedure

The procedure is similar to that described in Example 1, but starting with 3,4-methylenedioxybenzoic acid (16.6 g), N,N'-carbonyldiimidazole (16.2 g) and 2-amino-7-chloro-1,8-naphthyridine (11.7 g). The product produced by precipitation in water (15.7 g; m.p. 256° C.) is dissolved in 1-propanol (1000 cc). After 16 hours' cooling at 4° C., the crystallised solid is separated by filtration, washed with 1-propanol (3×20 cc) and dried at 40° C. under reduced pressure (0.067 kPa). N-(7-chloro-1,8-naphthyridin-2-yl)-3,4-methylenedioxybenzamide (8.4 g) is produced, m.p. 256° C.

Workup

  1. customthe crystallised solid is separated by filtration
  2. washwashed with 1-propanol (3×20 cc)
  3. customdried at 40° C. under reduced pressure (0.067 kPa)

Sources & evidence

ORD record
ord-6d2d2db60a1e4a6290f437f66107e198
Source dataset
uspto-grants-1987_02
Patent number
US04642308

Reaction notes

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