HCID 66692802, compound → HCID 66693638, compound

HRID 2367976Notes

Reaction equation

HRID 2367976 reaction equation
[Cl:1][C:2]1[C:10]2[CH:9]([CH2:11][N+:12]([O-])=O)[O:8][B:7]([OH:15])[C:6]=2[C:5]([O:16][CH2:17][CH2:18][CH2:19][OH:20])=[CH:4][CH:3]=1.[H][H]>N.[Ni]>[ClH:1].[NH2:12][CH2:11][CH:9]1[O:8][B:7]([OH:15])[C:6]2[C:5]([O:16][CH2:17][CH2:18][CH2:19][OH:20])=[CH:4][CH:3]=[C:2]([Cl:1])[C:10]1=2

Participants

5

Reactant 2

HCID 66692802HCID 66692802, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66693638HCID 66693638, compoundYield 241.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 222AmmoniaSolvent

Procedure

4-Chloro-7-(3-hydroxy-propoxy)-3-nitromethyl-3H-benzo[c][1,2]oxaborol-1-ol (105 mg, 0.35 mmol) in methanolic ammonia solution (2 M, 20 mL) was added Ra/Ni (0.15 g, 2800 Nickel slurry in water) and the reaction vessel was pressurized to 40 psi with hydrogen overnight at room temperature. The resultant mixture was filtered through a pad of Celite® and washed with EtOAc. The filtrate was concentrated in vacuo and the residue was added water (1 mL), followed by conc HCl to pH 1. The heterogeneous mixture was lyophilized provide the title compound (130 mg, quantitative) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.14 (br. s., 1H), 8.36 (br. s., 3H), 7.49 (d, J=8.2 Hz, 1H), 6.99 (d, J=8.2 Hz, 1 H), 5.40 (d, J=7.0 Hz, 1H), 4.40 (br. s., 1H), 4.10 (br. s., 2H), 3.59 (br. s., 2H), ˜3.30 (hidden, 1H), 2.89 (br. s., 1H), 1.89 (br. s, 2H); MS (ESI) m/z=272 (M+1, positive); HPLC purity: 96.92% (MaxPlot 200-400 nm), 97.96% (220 nm).

Workup

  1. filtrationThe resultant mixture was filtered through a pad of Celite®
  2. washwashed with EtOAc
  3. concentrationThe filtrate was concentrated in vacuo
  4. additionthe residue was added water (1 mL)

Sources & evidence

ORD record
ord-2b08d30af59d4bcbbf4ad65ae2f79c5d
Source dataset
uspto-grants-2014_04
Patent number
US08703742B2

Reaction notes

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