4-Chlorobenzylamine → HCID 178522950, compound

HRID 989665Notes

Reaction equation

HRID 989665 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 (0.27 g, 0.79 mmol) and 4-chlorobenzylamine (3.50 mL, 28.77 mmol) 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, 0.67 nmmol, 85%). Physical characteristics are as follows: m.p. 307-308° C.; 1H NMR (300 MHz, DMSO-d6) δ 9.99, 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, 0.67 nmmol, 85%)

Sources & evidence

ORD record
ord-789ef86fa0c14d628c5792ac32eb0270
Source dataset
uspto-grants-2002_10
Patent number
US06458788B1

Reaction notes

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