Triethylamine → HCID 12069561, compound

HRID 535461Notes

Reaction equation

HRID 535461 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][C:10]1[C:11]([CH3:19])=[CH:12][N:13]2[C:18]=1[CH:17]=[CH:16][CH:15]=[CH:14]2.[N+:20]([C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[CH:25][CH:24]=1)([O-:22])=[O:21].C(=O)([O-])O.[Na+]>ClC(Cl)C>[CH3:8][O:9][C:10]1[C:11]([CH3:19])=[C:12]([C:27]([C:26]2[CH:25]=[CH:24][C:23]([N+:20]([O-:22])=[O:21])=[CH:31][CH:30]=2)=[O:28])[N:13]2[C:18]=1[CH:17]=[CH:16][CH:15]=[CH:14]2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 113211231-methoxy-2-methylindolizine

Product 1

HCID 12069561HCID 12069561, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

1.8 ml (12.92 mmol) of triethylamine are added, at ambient temperature under an inert atmosphere, to 1.7 g (10.77 mmol) of 1-methoxy-2-methylindolizine in 15 ml of dichloroethane, followed, dropwise, by 2.2 g (11.85 mmol) of 4-nitrobenzoic acid chloride. The reaction medium is stirred for 30 minutes at ambient temperature, hydrolysed with a saturated aqueous solution of sodium hydrogen carbonate and then extracted with dichloromethane. The organic phase is washed with a saturated aqueous solution of sodium chloride, dried over sodium sulphate, and then concentrated under reduced pressure. The residue obtained is washed with diethyl ether. 3 g of an orange solid are obtained.

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic phase is washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue obtained
  6. washis washed with diethyl ether

Sources & evidence

ORD record
ord-496ba916cdec465bbfc0c7175f8647b2
Source dataset
uspto-grants-2014_10
Patent number
US08859544B2

Reaction notes

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