4-Chlorobenzylamine → HCID 178522950, compound

HRID 1168184Notes

Reaction equation

HRID 1168184 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([I:12])[CH:10]=2)[N:5]=[N:4][C:3]=1[C:13]([O:15]CC)=O.[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH2:24])=[CH:21][CH:20]=1>CCOC(C)=O>[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH:24][C:13]([C:3]2[N:4]=[N:5][C:6]3[C:11]([C:2]=2[OH:1])=[CH:10][C:9]([I:12])=[CH:8][CH:7]=3)=[O:15])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 660364-ChlorobenzylamineHCID 178470445HCID 178470445, compound

Product 1

HCID 178522950HCID 178522950, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl 4-hydroxy-6-iodo-3-cinnolinecarboxylate (Prep. 3, 0.27 g) and 4-chlorobenzylamine (3.50 mL) is heated at 90° C. for 30 minutes. The reaction is cooled slightly and poured into 25 mL EtOAc. Hexanes are added to precipitate the product and the resulting solid is filtered and dried. The product is further purified by trituration with CH2Cl2/hexanes (0.29 g, 85%). Physical characteristics are as follows: m.p. 307-308° C.; 1H NMR (300 MHz, DMSO-d6) δ9.99, 8.47, 8.15, 7.57, 7.40, 4.55; IR (drift) 2972, 2958, 2901, 2846, 1645, 1601, 1557, 1488, 1458, 1356, 933, 922, 822, 806, 722 cm−1; MS (ESI) m/z 439.8 (M+H)+, 437.8 (M−H)−; Anal. Calcd for C16H11ClIN3O2: C, 43.71; H, 2.52; N, 9.56; Found: C, 43.94; H, 2.50; N, 9.43.

Workup

  1. temperatureThe reaction is cooled slightly
  2. customto precipitate the product
  3. filtrationthe resulting solid is filtered
  4. customdried
  5. customThe product is further purified by trituration with CH2Cl2/hexanes (0.29 g, 85%)

Sources & evidence

ORD record
ord-68ef7f921fdd419ba0bdd1926e18d597
Source dataset
uspto-grants-2003_09
Patent number
US06624160B2

Reaction notes

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