2,6-Dichlorobenzaldehyde → 2-(2,6-Dichlorophenyl)imidazo[4,5-d]dipyrido[2,3-b:4',3'-f]azepin-3(8H)-ol

HRID 1043455Notes

Reaction equation

HRID 1043455 reaction equation
[N:1]1[C:6]2[NH:7][C:8]3[CH:18]=[N:17][CH:16]=[CH:15][C:9]=3/[C:10](=[N:13]/[OH:14])/[C:11](=O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C([O-])(=O)C.[NH4+:23].[Cl:24][C:25]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:26]=1[CH:27]=O>C(O)(=O)C>[Cl:24][C:25]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:26]=1[C:27]1[N:13]([OH:14])[C:10]2[C:9]3[CH:15]=[CH:16][N:17]=[CH:18][C:8]=3[NH:7][C:6]3[N:1]=[CH:2][CH:3]=[CH:4][C:5]=3[C:11]=2[N:23]=1

Participants

5

Reactant 3

HCID 67372,6-DichlorobenzaldehydeHCID 517165Ammonium AcetateHCID 178516816HCID 178516816, compound

Product 1

HCID 668867982-(2,6-Dichlorophenyl)imidazo[4,5-d]dipyrido[2,3-b:4',3'-f]azepin-3(8H)-olYield 93.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(6Z)-5H-dipyrido[2,3-b:4′,3′-f]azepine-5,6(11H)-dione 6-oxime (11.0 g, 0.0435 mol), ammonium acetate (50 g, 0.65 mol), 2,6-dichlorobenzaldehyde (15.2 g, 0.0870 mol) and acetic acid (200 mL) were heated at 90° C. for 30 minutes. The reaction was concentrated in vacuo to rigorously remove the acetic acid and then the residue was diluted with water (250 mL) and sodium bicarbonate saturated solution (250 mL) added to achieve a basic pH. Ethyl acetate (100 mL) and diethyl ether (300 mL) were then added. The desired product precipitated from the vigorously stirred mixture and was allowed to stand one hour prior to filtration that afforded the product as an off-yellow solid (16.1 g, 93%). This material was used without further purification in the next step. LCMS calculated for C19H12Cl2N5O (M+H)+: m/z=396. Elemental Analysis calculated for C19H13Cl4N5; C, 50.36; H, 2.89; Cl, 31.29; N, 15.45. Found: C, 48.93; H, 2.81; Cl, 30.57; N, 14.94.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customto rigorously remove the acetic acid
  3. additionthe residue was diluted with water (250 mL) and sodium bicarbonate saturated solution (250 mL)
  4. additionadded
  5. additionEthyl acetate (100 mL) and diethyl ether (300 mL) were then added
  6. customThe desired product precipitated from the vigorously stirred mixture
  7. filtrationto filtration

Sources & evidence

ORD record
ord-7cf4e7431e83425ab46c94e135d2ba60
Source dataset
uspto-grants-2013_10
Patent number
US08563541B2

Reaction notes

Loading…