Chloromethyl Methyl Ether → 7-(Methoxymethoxy)-8-nitroquinaldine

HRID 1920671Notes

Reaction equation

HRID 1920671 reaction equation
C(N(CC)CC)C.[OH:8][C:9]1[C:18]([N+:19]([O-:21])=[O:20])=[C:17]2[C:12]([CH:13]=[CH:14][C:15]([CH3:22])=[N:16]2)=[CH:11][CH:10]=1.[CH3:23][O:24][CH2:25]Cl>C1COCC1.C(Cl)(Cl)Cl>[CH3:23][O:24][CH2:25][O:8][C:9]1[C:18]([N+:19]([O-:21])=[O:20])=[C:17]2[C:12]([CH:13]=[CH:14][C:15]([CH3:22])=[N:16]2)=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 8471TriethylamineHCID 135858970HCID 135858970, compound

Product 1

HCID 252282437-(Methoxymethoxy)-8-nitroquinaldineYield 95.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

Referring to FIG. 20, triethylamine (174 μL, 1.695 mmol) was added to a solution of 5a (174 mg, 0.847 mmol) in dry THF (5 mL) under a nitrogen atmosphere. Chloromethyl methyl ether (128 μL, 1.695 mmol) was added to the mixture dropwise and the reaction was stirred for 1 h. The reaction was diluted with chloroform, washed with water followed by brine. The organic layer was dried over Na2SO4, and the solvent was evaporated to afford 8a (200 mg, 0.806 mmol, 95%) as a bright yellow solid: 1H NMR (CDCl3) δ 8.00 (1H, d, J=8.4 Hz), 7.81 (1H, d, J=9.2 Hz), 7.47 (1H, d, J=8.8 Hz), 7.26 (1H, d, J=8.4 Hz), 5.35 (2H, s), 3.52 (3H, s), 2.69 (3H, s); 13C NMR (CDCl3) δ 162.5, 148.3, 140.3, 137.7, 135.7, 130.3, 122.2, 122.2, 115.4, 95.3, 57.0, 25.9; FTIR (neat) 2955, 1626, 1525, 1508, 1377, 1247, 1226, 1193, 1153, 1065, 991, 924, 835, 806, 656 cm−1; MS (ESI) m/z calculated for (C12H12N2O4+H)+ 249, found 249; HRMS (ESI) m/z calculated for (C12H12N2O4+H)+ 249.0875, found 249.0871.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-8c2b86266cfb403896cea9855c7cb222
Source dataset
uspto-grants-2012_05
Patent number
US08173620B2

Reaction notes

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