Formaldehyde → HCID 14700579, compound

HRID 1084399Notes

Reaction equation

HRID 1084399 reaction equation
[F:1][C:2]1[C:20]([N:21]2[CH2:26][CH2:25][NH:24][CH:23]([CH3:27])[CH2:22]2)=[CH:19][C:5]2=[N:6][C:7]3[N:8]([CH3:18])[CH:9]=[C:10]([C:15]([OH:17])=[O:16])[C:11](=[O:14])[C:12]=3[CH:13]=[C:4]2[CH:3]=1.[CH2:28]=O.[OH-].[K+]>C(O)=O>[CH3:27][CH:23]1[N:24]([CH3:28])[CH2:25][CH2:26][N:21]([C:20]2[C:2]([F:1])=[CH:3][C:4]3[C:5]([CH:19]=2)=[N:6][C:7]2[N:8]([CH3:18])[CH:9]=[C:10]([C:15]([OH:17])=[O:16])[C:11](=[O:14])[C:12]=2[CH:13]=3)[CH2:22]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14797Potassium HydroxideHCID 14700559HCID 14700559, compound

Product 1

HCID 14700579HCID 14700579, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 1.15 g of 7-fluoro-1-methyl-8-(3-methyl-1-piperazinyl)-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid in 1.35 cm3 of 98% formic acid and 3.25 cm3 of a 30% aqueous formaldehyde solution is heated at a temperature close to 100° C. for 2 hours. The reaction mixture is concentrated under reduced pressure (20 kPa) at 50° C. and 5 cm3 of water are then added, the solution obtained is brought to pH 7 by adding 0.5 cm3 of 2 N aqueous potassium hydroxide solution and heated at a temperature close to 100° C. for 2 minutes. The product, which crystallizes, is drained at 20° C. and washed with twice 10 cm3 of water. The crude product obtained is recrystallized twice from 10 cm3 of dimethylformamide each time. 0.55 g of 8-(3,4-dimethyl-1-piperazinyl)-7-fluoro-1-methyl-4-oxo-1,4-dihydro-benzo[b][1,8] naphthyridine-3-carboxylic acid is obtained in the form of a yellow solid melting at 306°-308° C.

Workup

  1. customclose to 100° C. for 2 hours
  2. concentrationThe reaction mixture is concentrated under reduced pressure (20 kPa) at 50° C.
  3. addition5 cm3 of water are then added
  4. customthe solution obtained
  5. temperatureheated at a temperature
  6. customclose to 100° C. for 2 minutes
  7. customThe product, which crystallizes
  8. customis drained at 20° C.
  9. washwashed with twice 10 cm3 of water
  10. customThe crude product obtained
  11. customis recrystallized twice from 10 cm3 of dimethylformamide each time

Sources & evidence

ORD record
ord-b6702d2c9e544a82996efe313bce0493
Source dataset
uspto-grants-1991_04
Patent number
US05004745

Reaction notes

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