Formaldehyde → HCID 22380815, compound

HRID 895664Notes

Reaction equation

HRID 895664 reaction equation
[CH2:1]([N:3]1[C:11]2[CH2:10][CH2:9][N:8]([C:12]3[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][CH:15]=[CH:14][N:13]=3)[CH2:7][C:6]=2[N:5]=[CH:4]1)[CH3:2].C(N1C2CN(C3C([N+]([O-])=O)=CC=CN=3)CCC=2NC1)C.[CH2:41]=[O:42]>>[CH2:1]([N:3]1[C:11]2[CH2:10][CH2:9][N:8]([C:12]3[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][CH:15]=[CH:14][N:13]=3)[CH2:7][C:6]=2[N:5]=[C:4]1[CH2:41][OH:42])[CH3:2]

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 22380811HCID 22380811, compoundHCID 22380813HCID 22380813, compound

Product 1

HCID 22380815HCID 22380815, compound

Conditions

Temperature
150 °C

Procedure

A mixture of 1-ethyl-5-(3-nitro-pyridin-2-yl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine and 3-ethyl-5-(3-nitro-pyridin-2-yl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine in 37% formaldehyde (5 mL) in a sealed tube is heated at 150° C. overnight. The mixture is allowed to cool to ambient temperature and evaporated under reduced pressure. The resulting residue is partitioned between ethyl acetate and water and the layers are separated. The aqueous layer is further extracted with ethyl acetate and the combined organic extracts are dried over Na2SO4, filtered and the solvents removed under reduced pressure. Column chromatography of the residue on silica gel (5% MeOH in CH2Cl2 as eluent) gives [1-ethyl-5-(3-nitro-pyridin-2-yl)-4,5,6,7-tetrahydro-1H-imidazo [4,5-c]pyridin-2-yl]-methanol (80 mg). 1H NMR (CDCl3) δ: 8.33 (d, 1H), 8.15 (dd, 1H), 6.73 (q, 1H), 4.64 (s, 2H), 4.22 (s, 2H), 3.90-3.98 (m, 4H), 2.82(t, 2H) and 1.36 (t, 3H). MS: 304.2 (m+1).

Workup

  1. temperatureto cool to ambient temperature
  2. customevaporated under reduced pressure
  3. customThe resulting residue is partitioned between ethyl acetate and water
  4. customthe layers are separated
  5. extractionThe aqueous layer is further extracted with ethyl acetate
  6. dry with materialthe combined organic extracts are dried over Na2SO4
  7. filtrationfiltered
  8. customthe solvents removed under reduced pressure

Sources & evidence

ORD record
ord-793aaab7dae2412bb989e66be409135f
Source dataset
uspto-grants-2005_07
Patent number
US06916827B2

Reaction notes

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