Glutaric anhydride → HCID 58776025, compound

HRID 2067305Notes

Reaction equation

HRID 2067305 reaction equation
[OH:1][CH2:2][CH:3]1[C:15]2[CH:14]=[C:13]([NH2:16])[CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][C:6]([NH2:17])=[CH:7][CH:8]=2.[C:18]1(=[O:25])[O:24][C:22](=[O:23])[CH2:21][CH2:20][CH2:19]1.C1C=[C:30]2[C:32]([C:34]([OH:38])([OH:37])[C:35](=[O:36])[C:29]2=CC=1)=O.C(OCC)(=O)C.CO.C(O)(=O)C>O1CCCC1>[OH:1][CH2:2][CH:3]1[C:4]2[CH:5]=[C:6]([NH:17][C:35](=[O:36])[CH2:29][CH2:30][CH2:32][C:34]([OH:38])=[O:37])[CH:7]=[CH:8][C:9]=2[C:10]2[C:15]1=[CH:14][C:13]([NH:16][C:18](=[O:25])[CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[CH:12][CH:11]=2

Participants

6

Reactant 4

HCID 7940Glutaric anhydrideHCID 10236NinhydrinHCID 22023684HCID 22023684, compoundHCID 57447941(2,7-Diamino-9H-fluoren-9-yl)methanol

Product 1

HCID 58776025HCID 58776025, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
4 °C

Procedure

9-Hydroxymethyl-2,7-diaminofluorene (0.38 g, 1.7 mmol) was dissolved in anhydrous tetrahydrofuran (THF) (10 mL) and glutaric anhydride (97%, 2.2 eq, 3.7 mmol, 0.435 g) was added. The reaction was stirred for 4.5 hours and absence of amine was confirmed by TLC (ninhydrin stain, 90:10:3 ethyl acetate/methanol/acetic acid). The reaction mixture was diluted with hexanes (10 mL), filtered and washed with 1:1 THF/hexanes then hexanes. The crude product was dissolved in a minimal amount of methanol (1 mL) and THF (10 mL) and precipitated with addition of hexanes (10 mL). The mixture was cooled (4° C.), filtered and washed with 1:1 THF/Hexanes then hexanes. Yield was 0.59 g (77%) of yellow-orange powder. 1H-NMR (CD3OD): δ (ppm) 7.9 (s, 2H, Ar); 7.7 (d, 2H, Ar); 7.5 (dd, 2H, Ar); 4.0 (t, 1H, CH); 3.9 (d, 2H, CH2); 2.5 (t, 4H, CH2); 2.4 (t, 4H, CH2); 2.0 (m, 4H, CH2).

Workup

  1. filtrationfiltered
  2. washwashed with 1:1 THF/hexanes
  3. dissolutionThe crude product was dissolved in a minimal amount of methanol (1 mL) and THF (10 mL)
  4. customprecipitated with addition of hexanes (10 mL)
  5. filtrationfiltered
  6. washwashed with 1:1 THF/Hexanes

Sources & evidence

ORD record
ord-9bb5e5ecd5f844e496895a2ec6a640cf
Source dataset
uspto-grants-2012_10
Patent number
US08293869B2

Reaction notes

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