4-Chlorobenzylamine → HCID 178432387, compound

HRID 2227162Notes

Reaction equation

HRID 2227162 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[N:10][C:11]=1[CH3:12])[N:8]=[CH:7][C:6]([C:13]([O:15]CC)=O)=[C:5]2[OH:18].[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH2:25])=[CH:22][CH:21]=1>CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[N:10][C:11]=1[CH3:12])[N:8]=[CH:7][C:6]([C:13]([NH:25][CH2:24][C:23]1[CH:26]=[CH:27][C:20]([Cl:19])=[CH:21][CH:22]=1)=[O:15])=[C:5]2[OH:18]

Participants

4

Reactant 2

HCID 660364-ChlorobenzylamineHCID 178469685HCID 178469685, compound

Product 1

HCID 178432387HCID 178432387, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl 6-bromo-4-hydroxy-7-methyl[1,8]naphthyridine-3-carboxylate (Prep 1 0.57 g) and 4-chlorobenzylamine (2.59 g) is heated to 180° C. for 1 h. The mixture is cooled and diluted with EtOAc. The resulting precipitate is collected and dried. Physical characteristics are as follows: m.p. 269-270° C.; 1H NMR (DMSO-d6) δ 13.21, 10.09, 8.67, 8.62, 7.38, 4.54, 2.71; IR (drift) 3028, 2974, 2907, 1653, 1598, 1555, 1526, 1493, 1410, 1354, 1326, 1242, 1096, 806, 639 cm−1; Anal. Calcd for C17H13BrClN3O2: C, 50.21; H, 3.22; N, 10.33; Found: C, 50.31; H, 3.23; N, 10.17.

Workup

  1. temperatureThe mixture is cooled
  2. customThe resulting precipitate is collected
  3. customdried

Sources & evidence

ORD record
ord-8b640b2181cb4ae3a104316a4d7a6675
Source dataset
uspto-grants-2002_07
Patent number
US06413958B2

Reaction notes

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