3-Bromopropionic acid → 1,1,2-trimethyl[1H]-benz[e]indole-3-propanoic acid

HRID 1879603Notes

Reaction equation

HRID 1879603 reaction equation
[CH3:1][C:2]1([CH3:16])[C:10]2[C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[CH:7]=[CH:6][C:5]=2[N:4]=[C:3]1[CH3:15].Br[CH2:18][CH2:19][C:20]([OH:22])=[O:21]>ClC1C=CC=CC=1Cl>[CH3:1][C:2]1([CH3:16])[C:10]2[C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[CH:7]=[CH:6][C:5]=2[N:4]([CH2:18][CH2:19][C:20]([OH:22])=[O:21])[CH:3]1[CH3:15]

Participants

4

Reactant 2

HCID 115533-Bromopropionic acidHCID 1705302,3,3-Trimethylbenzoindolenine

Product 1

HCID 669869251,1,2-trimethyl[1H]-benz[e]indole-3-propanoic acidYield 112.2%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1,1,2-trimethyl[1H]-benz[e]indole (10.0 g, 47.8 mmol) and 3-bromopropanoic acid (7.3 g, 47.8 mmol) in 1,2-dichlorobenzene (50 mL) was heated with stirring at 110° C. for 18 h. After the resulting mixture was cooled to room temperature, the precipitated was collected by filtration, triturated with DCM thoroughly, and dried under vacuum to afford 15.2 g of light brown powder (88%). ESI-MS: observed for [MH]+281.31.

Workup

  1. temperaturewas heated
  2. temperatureAfter the resulting mixture was cooled to room temperature
  3. filtrationthe precipitated was collected by filtration
  4. customtriturated with DCM thoroughly
  5. customdried under vacuum

Sources & evidence

ORD record
ord-6b98eb3eef874f4598a57fcbdcc3693e
Source dataset
uspto-grants-2012_11
Patent number
US08318133B2

Reaction notes

Loading…