Sodium Carbonate → HCID 22921455, compound

HRID 2258411Notes

Reaction equation

HRID 2258411 reaction equation
[CH:1]([NH:4][OH:5])([CH3:3])[CH3:2].[C:6]([C:10]1[CH:17]=[CH:16][C:13]([CH2:14]Cl)=[CH:12][CH:11]=1)([O:8][CH3:9])=[O:7].C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[CH:1]([N:4]([CH2:14][C:13]1[CH:12]=[CH:11][C:10]([C:6]([O:8][CH3:9])=[O:7])=[CH:17][CH:16]=1)[OH:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 36664Methyl 4-(chloromethyl)benzoateHCID 78763Isopropylhydroxylamine

Product 1

HCID 22921455HCID 22921455, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

N-isopropylhydroxylamine (13.74 g, 90%, 165 mmol), 4-carbomethoxybenzyl chloride (30.4 g, 165 mmol) and Na2CO3 (18.0 g, 170 mmol) were dissolved in DMF (150 mL) and stirred at 60° C. under Argon for 20 h. The reaction mixture was filtered, concentrated, diluted with CHCl3 (300 mL), washed with water (3×200 mL), dried with MgSO4, concentrated, dissolved in EtOAC (10 mL) and chromatographed on an Si gel eluting with 4:1 hexanes/EtOAc to give 15.2 g (41%) N-isopropyl-N-(4-carbomethoxybenzyl)-hydroxylamine. 1H NMR (DMSO-d6) δ 7.85 (d, J=8.2 Hz, 2), 7.43 (d, J=8.2 Hz, 2), 7.44 (s, 1), 3.80 (s, 3), 3.73 (s, 1), 2.85 (sept, J=6.3 Hz, 1), 1.02 (d, J=6.3 Hz, 6). 13C{1H} NMR (DMSO-d6) δ 166.2, 145.6, 129.0, 128.8, 127.8, 59.3, 56.8, 52.0, 18.4.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. additiondiluted with CHCl3 (300 mL)
  4. washwashed with water (3×200 mL)
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated
  7. dissolutiondissolved in EtOAC (10 mL)
  8. customchromatographed on an Si gel
  9. washeluting with 4:1 hexanes/EtOAc

Sources & evidence

ORD record
ord-afc309c27ea94d7da14cb67d4e528f2f
Source dataset
uspto-grants-1997_08
Patent number
US05660974

Reaction notes

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