Acetyl chloride → HCID 86695916, compound

HRID 870920Notes

Reaction equation

HRID 870920 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15]3[C:10](=[C:11]([NH2:16])[N:12]=[CH:13][CH:14]=3)[CH2:9][O:8][C:6]=2[CH:7]=1.[C:17](Cl)(=[O:19])[CH3:18]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15]3[C:10](=[C:11]([NH:16][C:17](=[O:19])[CH3:18])[N:12]=[CH:13][CH:14]=3)[CH2:9][O:8][C:6]=2[CH:7]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 86695917HCID 86695917, compound

Product 1

HCID 86695916HCID 86695916, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 8-chloro-5H-chromeno[3,4-c]pyridin-4-amine (0.08 g, 0.344 mmol) in pyridine (5 mL) at 0° C. was added acetyl chloride (0.024 mL, 0.344 mmol) and the solution was stirred for 2 h. The volatile organics were removed under reduced pressure and the residue was diluted with water (5 mL). The reaction mixture was extracted with CH2Cl2 (2×15 mL). The combined organic extracts were washed with brine (1×10 mL), dried over sodium sulfate and concentrated under reduced pressure. The crude residue was taken to the next step without purification. LCMS (ESI) m/e 273 [(M)−, calcd for C14H10ClN2O2 273.1]; LC/MS retention time (Method C): tR=1.89 min.

Workup

  1. customThe volatile organics were removed under reduced pressure
  2. additionthe residue was diluted with water (5 mL)
  3. extractionThe reaction mixture was extracted with CH2Cl2 (2×15 mL)
  4. washThe combined organic extracts were washed with brine (1×10 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was taken to the next step without purification

Sources & evidence

ORD record
ord-f1287d3f661a4d6f8d77cbb14b78155a
Source dataset
uspto-grants-2015_03
Patent number
US08969564B2

Reaction notes

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