Toluene → HCID 57457834, compound

HRID 44783Notes

Reaction equation

HRID 44783 reaction equation
[NH2:1][C:2]1[CH2:3][N:4](NCC2(O)CCCC2)[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.C([O:27][CH2:28][CH3:29])(OCC)OCC.Cl.[N:31]1[CH:36]=CC=C[CH:32]=1.[C:37]1(C)[CH:42]=CC=C[CH:38]=1>>[N:31]1([CH2:36][C:28]2([OH:27])[CH2:29][CH2:42][CH2:37][CH2:38]2)[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=[CH:32]1

Participants

5

Reactant 4

HCID 1140TolueneHCID 31214Ethyl orthoformateHCID 10176127Pyridinium chlorideHCID 66919169HCID 66919169, compound

Product 1

HCID 57457834HCID 57457834, compound

Procedure

A mixture of 1-{{(3-aminoquinolin-1-yl)amino]methyl}cyclopentanol (2.00 g, 7.8 mmol, Example 3 Parts A through D), triethyl orthoformate (1.36 mL, 8.2 mmol), pyridine hydrochloride (0.2 g), and toluene (20 mL) was heated at reflux for 3.5 hours. The reaction mixture was allowed to cool to ambient temperature. A solid was isolated by filtration and dried. The solid was triturated with a minimum amount of saturated aqueous sodium bicarbonate for 1 hour. The solid was filtered and then dried to provide 1.85 g of 1-[(1H-imidazo[4,5-c]quinolin-1-yl)methyl]cyclopentanol as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3.5 hours
  3. customA solid was isolated by filtration
  4. customdried
  5. customThe solid was triturated with a minimum amount of saturated aqueous sodium bicarbonate for 1 hour
  6. filtrationThe solid was filtered
  7. customdried

Sources & evidence

ORD record
ord-30cb8176536b4207a7520ae2101c6c4c
Source dataset
uspto-grants-2013_09
Patent number
US08541438B2

Reaction notes

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