Hydrochloric Acid → Indeno[1,2-b]fluorene, 6,12-dihydro-

HRID 1488318Notes

Reaction equation

HRID 1488318 reaction equation
[OH-].[K+].[CH:3]1[C:15]2[C:14](=O)[C:13]3[CH:12]=[C:11]4[C:17]5[C:22]([C:23](=O)[C:10]4=[CH:9][C:8]=3[C:7]=2[CH:6]=[CH:5][CH:4]=1)=[CH:21][CH:20]=[CH:19][CH:18]=5.O.NN.Cl>C(O)COCCO>[CH:21]1[C:22]2[CH2:23][C:10]3[CH:9]=[C:8]4[C:7]5[C:15]([CH2:14][C:13]4=[CH:12][C:11]=3[C:17]=2[CH:18]=[CH:19][CH:20]=1)=[CH:3][CH:4]=[CH:5][CH:6]=5

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 144708915695-13-6

Product 1

HCID 15559295Indeno[1,2-b]fluorene, 6,12-dihydro-

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Conditions

Temperature
170 °C

Procedure

Potassium hydroxide (163.7 g), diethylene glycol (1412 mL, Alfa-Aesar) and indeno[1,2-b]fluorene-6,12-dione (28.23 g) were charged to a suitable vessel under argon. Hydrazine-hydrate (152 mL, Alfa-Aesar) was added and the reaction heated to 170° C. for 18 hours. The reaction mixture was slowly added to a mixture of ice (2 kg) and concentrated hydrochloric acid (1 L) and the resulting slurry stirred for 10 minutes. The solids were collected by vacuum filtration, washed with water (3×500 mL) and dried to give the product as a grey solid. Yield; 24.49 g. 1H NMR (400 MHz, CDCl3); 7.95 (2H, m), 7.80 (2H, m), 7.54 (2H, m), 7.39 (2H, m), 7.30 (2H, m).

Workup

  1. filtrationThe solids were collected by vacuum filtration
  2. washwashed with water (3×500 mL)
  3. customdried

Sources & evidence

ORD record
ord-c6679efe95284265a493f7bfce77ef6b
Source dataset
uspto-grants-2016_08
Patent number
US09431145B2

Reaction notes

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