4-Chlorobenzylamine → HCID 178522886, compound

HRID 2290016Notes

Reaction equation

HRID 2290016 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]=[CH:7][C:6]([C:13]([OH:15])=O)=[C:5]2[OH:16].C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][NH2:35])=[CH:32][CH:31]=1>CC(N(C)C)=O.O>[Cl:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][NH:35][C:13]([C:6]2[CH:7]=[N:8][C:9]3[C:4]([C:5]=2[OH:16])=[CH:3][C:2]([F:1])=[C:11]([F:12])[CH:10]=3)=[O:15])=[CH:32][CH:31]=1

Participants

7

Reactant 3

HCID 660364-ChlorobenzylamineHCID 682631,1'-CarbonyldiimidazoleHCID 178524725HCID 178524725, compound

Product 1

HCID 178522886HCID 178522886, compound

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 0.5 g of 6,7-difluoro-4-hydroxy-3-quinolinecarboxylic acid from preparation No. 15 and 0.435 g of carbonyldiimidazole in 8 mL of anhydrous dimethylacetamide is stirred 4 h at 65° C. The reaction mixture is cooled to 25° C. and 2 drops of distilled water is added. After an additional 10 min 0.34 mL of 4-chlorobenzylamine is added. The mixture is stirred 26 h at 25° C. and then diluted with 10 mL of distilled water. After standing for an additional 30 min the precipitate is collected by filtration and washed with three 10 mL portions of distilled water. The solid is dried in a stream of air and then at 20 torr/120° C./3 days. The yield is 0.51 g (70%) of a white solid.

Workup

  1. customfrom preparation No
  2. waitAfter standing for an additional 30 min
  3. filtrationthe precipitate is collected by filtration
  4. washwashed with three 10 mL portions of distilled water
  5. customThe solid is dried in a stream of air
  6. customat 20 torr/120° C./3 days

Sources & evidence

ORD record
ord-d4a790c84a0b458589ecdf4ad9888980
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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