Fluorescein 5-isothiocyanate → 2-(6-Hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid

HRID 2390607Notes

Reaction equation

HRID 2390607 reaction equation
[CH:1]1[C:6](N=C=S)=[CH:5][C:4]2[C:10]([O:12][C:13]3([C:23]4[CH:24]=[CH:25][C:26]([OH:28])=[CH:27][C:22]=4[O:21][C:15]4[CH:16]=[C:17]([OH:20])[CH:18]=[CH:19][C:14]3=4)[C:3]=2[CH:2]=1)=[O:11].CCN(C(C)C)C(C)C>CN(C=O)C>[CH:1]1[CH:6]=[CH:5][C:4]([C:10]([OH:12])=[O:11])=[C:3]([C:13]2[C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]=3[O:21][C:22]3[C:23]=2[CH:24]=[CH:25][C:26]([CH:27]=3)=[O:28])[CH:2]=1

Participants

4

Reactant 2

HCID 18730Fluorescein 5-isothiocyanateHCID 81531Diisopropylethylamine

Product 1

HCID 33832-(6-Hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acidYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The amine (11.3 mg, 23 μmol) was combined with fluorescein isothiocyanate (10.4 mg, 35 μmol) and DIEA (12 μL, 69 μmol) in DMF (400 μL). The solution was stirred 1.5 h and concentrated. The product was purified using HPLC (gradient 50-70% ACN/H2O) to yield 11 as an orange solid (16.2 mg, 18.5 μmol) in 80% yield. 1H (300 MHz, CD3OD): δ 8.11 (s, 1H), 7.70 (d, 1H, J=8.1 Hz), 7.51 (d, 2H, J=7.8 Hz), 7.20 (s, 4H), 7.15 (d, 2H, J=8.5 Hz), 7.08 (d, 1H, J=8.2 Hz), 6.71 (d, 2H, J=8.5 Hz), 6.68 (d, 2H, J=2.1 Hz), 6.54 (dd, 2H, J=8.8, 2.4 Hz), 4.66 (dd, 1H, J=8.4, 5.0 Hz), 3.53 (m, 2H), 3.30 (dd, 1H, J=14.4, 5.0 Hz), 3.05 (dd, 1H, J=14.0, 8.2 Hz), 2.56 (t, 2H, J=7.8 Hz), 1.60-1.57 (m, 4H), 1.31 (br s, 8H); 13C (75 mHz, CD3OD): δ 182.5, 173.4, 170.4, 170.1, 154.6, 136.5, 133.6, 131.8, 130.5, 129.6, 129.3, 126.9, 126.0, 114.1, 144.0, 103.2, 60.4, 60.3, 37.7, 36.3, 32.1, 30.1, 30.0, 29.8, 29.6, 27.6; LC/MS (ESI) (m/z) [M+H]+ calcd 875.3. found 875.3.

Workup

  1. concentrationconcentrated
  2. customThe product was purified

Sources & evidence

ORD record
ord-f5f7e87739f24cbc9cd8c69d84dbb3b8
Source dataset
uspto-grants-2012_09
Patent number
US08273778B2

Reaction notes

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