Dichloromethane → HCID 19026199, compound

HRID 1195168Notes

Reaction equation

HRID 1195168 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[C:8]1([CH2:14][O:15][NH:16][CH:17]2[CH2:26][CH2:25][CH2:24][C:23]3[N:22]=[C:21]([O:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH:20]=[CH:19][C:18]2=3)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Cl:35]CCl>>[ClH:35].[C:8]1([CH2:14][O:15][N:16]([CH:17]2[CH2:26][CH2:25][CH2:24][C:23]3[N:22]=[C:21]([O:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH:20]=[CH:19][C:18]2=3)[C:1](=[O:3])[CH3:2])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 3

HCID 6344Dichloromethane2×HCID 7918Acetic AnhydrideHCID 19026180HCID 19026180, compound

Product 1

HCID 19026199HCID 19026199, compoundYield 52%

Procedure

Acetic anhydride (3.77 g) was added to a solution of N,N-dimethylaminopyridine (0.2 g), N,2-bis(phenylmethoxy)-5,6,7,8-tetrahydro-5-quinolinamine (12.1 g) and dichloromethane (170 ml) at room temperature. The mixture was stirred at room temperature for 48 hrs, diluted with dichloromethane, and extracted with saturated sodium bicarbonate solution. The combined extracts were washed with water, brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. The residue was dissolved in methanol and acidified with 2-propanol/hydrochloric acid solution. The mixture was evaporated and the residue was recrystallized from ethanol/ethyl acetate to give 7.64 g (52%) of product, mp 125°-126° C.

Workup

  1. extractionextracted with saturated sodium bicarbonate solution
  2. washThe combined extracts were washed with water, brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. dissolutionThe residue was dissolved in methanol
  7. customThe mixture was evaporated
  8. customthe residue was recrystallized from ethanol/ethyl acetate

Sources & evidence

ORD record
ord-3480d9b52d8d4b10955def8351d43e97
Source dataset
uspto-grants-1992_05
Patent number
US05110815

Reaction notes

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