Sodium Hydroxide → HCID 86749201, compound

HRID 374975Notes

Reaction equation

HRID 374975 reaction equation
C1(C[N:8](CC2C=CC=CC=2)[C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:18]=2[N:17]=[CH:16][C:15]2[N:19]=[C:20]4[CH2:25][CH2:24][CH2:23][CH2:22][N:21]4[C:14]3=2)C=CC=CC=1.[OH-].[Na+]>C(O)=O.C(Cl)Cl.[OH-].[OH-].[Pd+2]>[CH:12]1[CH:11]=[CH:10][C:9]([NH2:8])=[C:18]2[C:13]=1[C:14]1[N:21]3[CH2:22][CH2:23][CH2:24][CH2:25][C:20]3=[N:19][C:15]=1[CH:16]=[N:17]2

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 67771606HCID 67771606, compound

Product 1

HCID 86749201HCID 86749201, compoundYield 32.6%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 284Formic AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

Palladium hydroxide on carbon (0.35 g) was added to a solution of N,N-bis(phenylmethyl)-8,9,10,11 tetrahydropyrido[1',2':1,2]imidazo[4,5-c]quinolin-4-amine (0.38 g, 0.9 mmole) in formic acid (about 15 mL). The reaction mixture was heated at reflux for 3 days then diluted with methylene chloride and made basic (about pH 9) with 10% sodium hydroxide. The methylene chloride layer was separated, dried over magnesium sulfate and then concentrated under vacuum to provide a white solid. The material was purified by column chromatography (silica gel eluting with 4-10% methanol in methylene chloride v/v) to provide a solid. The solid was suspended in methylene chloride (20 mL) then isolated by filtration and dried to provide 70 mg of 8,9,10,11 tetrahydropyrido[1',2':1,2]imidazo[4,5-c]quinolin-4-amine as a solid, m.p. 275°-278° C. Calculated for C14H14N4 +0.2 CH2Cl2 : %C, 66.81; %H, 5.69; %N, 21.95; Found: %C, 67.06; %H, 5.60; %N, 22.18.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 days
  3. customThe methylene chloride layer was separated
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. customto provide a white solid
  7. customThe material was purified by column chromatography (silica gel eluting with 4-10% methanol in methylene chloride v/v)
  8. customto provide a solid
  9. customthen isolated by filtration
  10. customdried

Sources & evidence

ORD record
ord-c63dbbc955244588b4aab7d36a509e0c
Source dataset
uspto-grants-1996_01
Patent number
US05482936

Reaction notes

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