Hydrochloric Acid → HCID 58473556, compound

HRID 2282344Notes

Reaction equation

HRID 2282344 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)[C:5]([CH2:17][CH2:18][CH2:19][CH2:20][N:21]3C(=O)C4C(=CC=CC=4)C3=O)([CH3:16])[C:4]=2[CH:3]=1.O.NN.Cl.ClCCl>C(O)C>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)[C:5]([CH2:17][CH2:18][CH2:19][CH2:20][NH2:21])([CH3:16])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 24654Hydrazine hydrate (1:1)HCID 58473621HCID 58473621, compound

Product 1

HCID 58473556HCID 58473556, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

2-(4-(2,7-dibromo-9-methyl-9H-fluoren-9-yl)butyl)isoindoline-1,3-dione (3.08, 5.71 mmol) was dissolved in ethanol (250 mL) under nitrogen. To the mixture was added hydrazine monohydrate (2.77 mL, 57.1 mmol), and the reaction was refluxed at 80° C. for 3.0 hours. The reaction was cooled to room temperature, and added 1M HCl (˜100 mL). The mixture was stirred for 30 minutes or until all solids were dissolved. Dichloromethane was added to the solution and the organic layer was extracted with saturated NaHCO3 three times, and washed with water. The organic layers were collected and removed solvent by vacuo to give an yellow oil (2.33 g, 100%). 1H NMR (500 MHz, CD2Cl2): δ=7.57 (d, 2H), 7.52 (d, 2H), 7.46-7.48 (dd, 2H), 2.39-2.42 (t, 2H), 1.95-1.98 (t, 2H), 1.44 (s, 3H), 1.17-1.23 (m, 2H), 0.59-0.65 (m, 2H).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. dissolutionwere dissolved
  3. extractionthe organic layer was extracted with saturated NaHCO3 three times
  4. washwashed with water
  5. customThe organic layers were collected
  6. customremoved solvent by vacuo

Sources & evidence

ORD record
ord-a87bf8dc10e4447e9dc1574487622e1b
Source dataset
uspto-grants-2015_09
Patent number
US09139869B2

Reaction notes

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