Hydrochloric Acid → HCID 66700039, compound

HRID 1910730Notes

Reaction equation

HRID 1910730 reaction equation
[C:1](=[O:25])([O:3][CH:4]1[C:13]2[CH:12]=[C:11]3[O:14][CH:15]([CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[O:16][C:10]3=[CH:9][C:8]=2[NH:7][CH:6]([CH3:24])[CH2:5]1)[NH2:2].N1C=CC=CC=1.[C:32](Cl)(=[O:34])[CH3:33].Cl>ClCCl>[C:1](=[O:25])([O:3][CH:4]1[C:13]2[CH:12]=[C:11]3[O:14][CH:15]([CH2:17][C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[O:16][C:10]3=[CH:9][C:8]=2[N:7]([C:32](=[O:34])[CH3:33])[CH:6]([CH3:24])[CH2:5]1)[NH2:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6367Acetyl chlorideHCID 66700221HCID 66700221, compound

Product 1

HCID 66700039HCID 66700039, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[Step 3] 675 mg (approx. 1.98 mmol) of the benzyl-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]quinolin-8-yl carbamate were dissolved in 15 mL of dichloromethane followed by adding 313 mg (4.0 mmol) of pyridine. 234 mg (3.0 mmol) of acetyl chloride were further added followed by stirring for 30 minutes at room temperature. Following completion of the reaction, aqueous hydrochloric acid (1 mol/L) was added followed by extraction with chloroform. The organic phase was washed with water and then dehydrated with anhydrous sodium sulfate. The solution was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate 2:1) to obtain 367 mg of benzyl-5-acetyl-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]quinolin-8-yl carbamate in the form of a pale brown oil (56%, 2 steps).

Workup

  1. additionwas added
  2. extractionfollowed by extraction with chloroform
  3. washThe organic phase was washed with water
  4. concentrationThe solution was concentrated under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate 2:1)

Sources & evidence

ORD record
ord-36ee50985d494a48b0b9348df20e88e0
Source dataset
uspto-grants-2013_12
Patent number
US08604030B2

Reaction notes

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