4-Nitroaniline → HCID 13450497, compound

HRID 1876862Notes

Reaction equation

HRID 1876862 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].O1CCCC1.[CH2:16]([CH2:22]Cl)[CH2:17][O:18][C:19](Cl)=[O:20].CC(C)([O-])C.[K+]>CN(C)C1C=CN=CC=1>[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([N:8]2[CH2:22][CH2:16][CH2:17][O:18][C:19]2=[O:20])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 74754-NitroanilineHCID 8028Tetrahydrofuran2×HCID 69399Carbonochloridic acid, 3-chloropropyl esterHCID 23665647Potassium tert-butoxide

Product 1

HCID 13450497HCID 13450497, compoundYield 32.5%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a mixture of p-nitroaniline (0.50 g, 0.0036 mol) and 4-dimethylaminopyridine (DMAP, 0.531 g, 0.00434 mol) in tetrahydrofuran (10 mL, 0.1 mol) was added 3-chloropropyl chloridocarbonate (0.480 mL, 0.00398 mol). The mixture was stirred at room temperature for 1 h, then treated with 1.0 M of potassium tert-butoxide in tetrahydrofuran (7.96 mL, 0.00796 mol) at room temperature for 2 h, then quenched with aqueous ammonium chloride, extracted with EtOAc. The combined organic layers were washed with water, brine, dried and evaporated to dryness. The residue was purified on silica gel, eluting with 0 to 10% MeOH in dichloromethane, to provide the product (260 mg, 32.32%). LCMS (M+H) 222.9.

Workup

  1. customquenched with aqueous ammonium chloride
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with water, brine
  4. customdried
  5. customevaporated to dryness
  6. customThe residue was purified on silica gel
  7. washeluting with 0 to 10% MeOH in dichloromethane

Sources & evidence

ORD record
ord-b31a4ba62eb74f43b20b0ce57877cc6f
Source dataset
uspto-grants-2012_11
Patent number
US08309718B2

Reaction notes

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