Hydrochloric Acid → HCID 86669350, compound

HRID 924968Notes

Reaction equation

HRID 924968 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1[OH:10])[CH:5]=[O:6].C([O-])([O-])=O.[Cs+].[Cs+].[Na+].[I-].Br[CH:23]([CH3:25])[CH3:24].Cl>CN(C=O)C.CCOC(C)=O>[OH:10][C:9]1[C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[O:1][CH:23]([CH3:25])[CH3:24]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 63582-BromopropaneHCID 10796Cesium carbonateHCID 57489573,4-Dihydroxy-5-nitrobenzaldehyde

Product 1

HCID 86669350HCID 86669350, compoundYield 18.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 3,4-dihydroxy-5-nitrobenzaldehyde (1.0 g, 5.46 mmol) in dry DMF (10 mL) was added Cs2CO3 (3563 mg, 10.93 mmol), NaI (819 mg, 5.46 mmol) and 2-bromopropane (1009 mg, 8.20 mmol) and the mixture was stirred at 60° C. overnight. The mixture was cooled to room temperature and added 1N HCl till pH=7, followed by a standard aqueous/EtOAc workup. The residue was purified by silica gel column chromatography (DCM:THF=20:1) to give Intermediate 49 as a yellow solid (230 mg, 18.7%). 1H NMR (DMSO-d6 500 MHz TMS): δ 9.86 (s, 1H), 8.08 (s, 1H), 7.65 (s, 1H), 4.79 (m, 1H), 1.28 (d, J=6.5 Hz, 6H).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customThe residue was purified by silica gel column chromatography (DCM:THF=20:1)

Sources & evidence

ORD record
ord-d24b41090d934b1f9451980f871b46c5
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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