Pyridine → 9-Nitro-9,10-dihydro-11-methyl-9,10-ethanoanthracene-11-carboxylic acid fluoride

HRID 900821Notes

Reaction equation

HRID 900821 reaction equation
[N+:1]([C:4]12[CH2:19][C:18]([CH3:23])([C:20](O)=[O:21])[CH:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=31)[C:10]1[C:5]2=[CH:6][CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].N1C=CC=CC=1.N1C(F)=NC(F)=NC=1[F:32]>C(Cl)Cl.Cl>[N+:1]([C:4]12[CH2:19][C:18]([CH3:23])([C:20]([F:32])=[O:21])[CH:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=31)[C:10]1[C:5]2=[CH:6][CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 12664Cyanuric fluorideHCID 596985749-Nitro-9,10-dihydro-11-methyl-9,10-ethanoanthracene-11-carboxylic acid

Product 1

HCID 586702979-Nitro-9,10-dihydro-11-methyl-9,10-ethanoanthracene-11-carboxylic acid fluorideYield 98%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 9-nitro-9,10-dihydro-11-methyl-9,10-ethanoanthracene-11-carboxylic acid (hereafter called Core C) (500 mg, 1.6 mmol) and pyridine (0.25 mL, 3.0 mmol) in 10 mL of DCM was added a solution of cyanuric fluoride (400 mg, 3.0 mmol) dropwise. After stirring 30 min, the reaction was diluted with 1N HCl, and extracted 2×DCM. The DCM extracts were dried over MgSO4. The solution was filtered, concentrated by rotary evaporator to give 482 mg (98%) of 9-nitro-9,10-dihydro-11-methyl-9,10-ethanoanthracene-11-carboxylic acid fluoride Core D. MS found: (M+H)+=312.

Workup

  1. extractionextracted 2×DCM
  2. dry with materialThe DCM extracts were dried over MgSO4
  3. filtrationThe solution was filtered
  4. concentrationconcentrated by rotary evaporator

Sources & evidence

ORD record
ord-6193aede679c47c0891254c1f9a2d275
Source dataset
uspto-grants-2008_04
Patent number
US07361654B2

Reaction notes

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