Methanol → Anthracene

HRID 237177

Reaction equation

HRID 237177 reaction equation
N1C(C(Cl)=O)=CC=CC=1C(Cl)=O.NC[C:15]1[C:16]2[C:21]([C:22](CN)=[C:23]3[C:28]=1[CH:27]=[CH:26][CH:25]=[CH:24]3)=[CH:20][CH:19]=[CH:18][CH:17]=2.C(N(CC)CC)C.CO>C(Cl)(Cl)Cl>[CH:17]1[C:16]2[C:21](=[CH:22][C:23]3[C:28]([CH:15]=2)=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 773352,6-Pyridinedicarbonyl dichlorideHCID 11481774Anthracene-9,10-dimethanamine

Product 1

HCID 8418Anthracene

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent4×

Procedure

Clear solutions of 2,6-pyridinedicarbonyl dichloride (84 mg, 0.41 mmol) in 15 mL of chloroform and 9,10-bis(aminomethyl)anthracene (97 mg, 0.41 mmol) in 15 mL of chloroform were simultaneously added dropwise over 10 h to a stirred solution of squaraine 13a (32 mg, 0.05 mmol, synthesized according to E. Arunkumar et al. Chem. Eur. J. 2006, 12, 4884-4690) and triethylamine (81 mg, 0.8 mmol) in 30 mL of chloroform. After overnight stirring, the mixture containing rotaxane 13 and polymer co-products was filtered, washed with chloroform (100 mL) to extract rotaxane 13, and the filtrate was concentrated. Purification of the crude material by column chromatography using silica gel (gradient, 0-1% of MeOH in CHCl3) gave the rotaxane 13. λmax (abs): 651 m, λmax (em): 707 nm, 59% (methanol); λmax (abs): 648 nm, λmax (em): 700 nm, Q.Y.: 65% (chloroform).

Workup

  1. additionthe mixture containing rotaxane 13 and polymer co-products
  2. filtrationwas filtered
  3. washwashed with chloroform (100 mL)
  4. extractionto extract rotaxane 13
  5. concentrationthe filtrate was concentrated
  6. customPurification of the crude material by column chromatography
  7. customgave the rotaxane 13

Sources & evidence

ORD record
ord-fd0c4243253a42aca4db30ba11b3a6d1
Source dataset
uspto-grants-2014_02
Patent number
US08642014B2

Linked notes

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