Acetyl chloride → 1-(3,3-Dimethyl-6-nitroindolin-1-yl)ethanone

HRID 470656Notes

Reaction equation

HRID 470656 reaction equation
[CH3:1][C:2]1([CH3:14])[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[NH:4][CH2:3]1.CCN(CC)CC.[C:22](Cl)(=[O:24])[CH3:23]>O>[CH3:1][C:2]1([CH3:14])[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[N:4]([C:22](=[O:24])[CH3:23])[CH2:3]1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 219594663,3-Dimethyl-6-nitroindoline

Product 1

HCID 161274181-(3,3-Dimethyl-6-nitroindolin-1-yl)ethanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
22.5 °C

Procedure

A solution of 3,3-dimethyl-6-nitroindoline (Example 4, 190.5 g) in 1200 mL IPAC, Et3N (200.6 g) was charged to a 1-L jacketed reactor, followed by the drop-wise addition of acetyl chloride (155.4 g) while maintaining reaction temperature<25° C. The reaction contents were stirred for 1 h at 20-25° C. 1200 mL D.I. water was charged slowly at T<30° C. to form a suspension. The product was isolated by filtration. Wet cake was washed with D.I. water (200 mL×2) and heptane (200 mL), and was dried at 50° C. under vacuum until constant weight. (193 g, 83.2 wt % adjusted yield, 99.15 A %, 99.5 wt % (dry))

Workup

  1. temperaturewhile maintaining
  2. customreaction temperature<25° C
  3. customThe reaction contents
  4. customto form a suspension
  5. customThe product was isolated by filtration
  6. washWet cake was washed with D.I
  7. dry with materialwater (200 mL×2) and heptane (200 mL), and was dried at 50° C. under vacuum until constant weight
  8. custom(193 g, 83.2 wt % adjusted yield
  9. custom99.15 A %, 99.5 wt % (dry))

Sources & evidence

ORD record
ord-c6dc6292a01f47269daaf8809e5c4229
Source dataset
uspto-grants-2014_01
Patent number
US08629289B2

Reaction notes

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