Formaldehyde → N-[(4-Chlorophenyl)methyl]-7-(dimethylamino)-4-hydroxy-3-quinolinecarboxamide

HRID 2289914Notes

Reaction equation

HRID 2289914 reaction equation
[C:1]([BH3-])#[N:2].[Na+].N[C:6]1[CH:15]=[C:14]2[C:9]([C:10]([OH:27])=[C:11]([C:16]([NH:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)=[O:17])[CH:12]=[N:13]2)=[CH:8][CH:7]=1.[CH2:28]=O>C(O)(=O)C.O>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][NH:18][C:16]([C:11]2[CH:12]=[N:13][C:14]3[C:9]([C:10]=2[OH:27])=[CH:8][CH:7]=[C:6]([N:2]([CH3:1])[CH3:28])[CH:15]=3)=[O:17])=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 178507324HCID 178507324, compound

Product 1

HCID 178482605N-[(4-Chlorophenyl)methyl]-7-(dimethylamino)-4-hydroxy-3-quinolinecarboxamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

Sodium cyanoborohydride (96 mg) is added to a mixture of 100 mg 7-amino-N-[(4-chlorophenyl)methyl]-4-hydroxy-3-quinolinecarboxamide and 91 mg paraformaldehyde in 5 mL of acetic acid. After 2 days the mixture is diluted with 5 mL of distilled water (use of more water causes the product to precipitate as an oil). The mixture is stirred an additional 10 min and then the product is collected by filtration. It is washed with three 1 mL portions of 50% aqueous acetic acid and dried in a stream of air. It is dried at 20 torr/24 h/75° C. The product is obtained as mg of an off-white powder.

Workup

  1. customto precipitate as an oil)
  2. filtrationthe product is collected by filtration
  3. washIt is washed with three 1 mL portions of 50% aqueous acetic acid
  4. customdried in a stream of air
  5. customIt is dried at 20 torr/24 h/75° C
  6. customThe product is obtained as mg of an off-white powder

Sources & evidence

ORD record
ord-57c1d3e902b744e98b224443f64b98d0
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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