Isopropanol → HCID 13579406, compound

HRID 235817Notes

Reaction equation

HRID 235817 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=O.[NH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[N:16][C:17]([Cl:23])=[CH:18][CH:19]=2)[N:14]=1.CC(O)C>O>[Cl:23][C:17]1[N:16]=[C:15]2[C:20]([CH:21]=[CH:22][C:13]([NH:12][C:6](=[O:8])[C:5]3[CH:9]=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=3)=[N:14]2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 114613-Methoxybenzoic AcidHCID 851997-Chloro-1,8-naphthyridin-2-amine

Product 1

HCID 13579406HCID 13579406, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
4 °C

Procedure

The procedure is similar to that described in Example 1, but starting with 3-methoxybenzoic acid (12.17 g), N,N'-carbonyldiimidazole (12.9 g) and 2-amino-7-chloro-1,8-naphthyridine (8.9 g). The product produced by precipitation in water (15.5 g; m.p. 176° C.) is dissolved in boiling 2-propanol (500 cc). After 2 hours' cooling at 4° C., the crystallised solid is separated by filtration, washed with 2-propanol (3×25 cc) and dried at 40° C. under reduced pressure (0.067 kPa). N-(7-chloro-1,8-naphthyridin-2-yl)-3-methoxybenzamide (11.2 g) is produced, m.p. 178° C.

Workup

  1. dissolutionis dissolved
  2. customthe crystallised solid is separated by filtration
  3. washwashed with 2-propanol (3×25 cc)
  4. customdried at 40° C. under reduced pressure (0.067 kPa)

Sources & evidence

ORD record
ord-bdb7f8bdb88e4cb892d940dffdb5b82b
Source dataset
uspto-grants-1987_02
Patent number
US04642308

Reaction notes

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