Morpholine → 5-Morpholino-2-nitroaniline

HRID 1777764Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl[C:8]1[CH:9]=[CH:10][C:11]([N+:15]([O-:17])=[O:16])=[C:12]([CH:14]=1)[NH2:13]>CN(C=O)C>[N:1]1([C:8]2[CH:9]=[CH:10][C:11]([N+:15]([O-:17])=[O:16])=[C:12]([NH2:13])[CH:14]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of morpholine (0.88 mL) and 5-chloro-2-nitroaniline (1.76 g) in DMF (50 mL) was added TEA (2.78 mL). The mixture was stirred at 120° C. overnight, cooled down and the solvent was removed in vacuo. The residue was purified by CC (Biotage, SNAP 50 g cartridge, solvent A: Hept; solvent B: EA; gradient in % B: 10 for 3CV, 10 to 30 over 6CV, 30 for 2CV, 30 to 50 over 4CV, 50 for 6CV) to afford 380 mg of yellow powder. LC-MS (B): tR=0.69 min; [M+H]+: 224.15.

Workup

temperaturecooled down
customthe solvent was removed in vacuo
customThe residue was purified by CC (Biotage, SNAP 50 g cartridge, solvent A: Hept; solvent B: EA; gradient in % B: 10 for 3CV, 10 to 30 over 6CV, 30 for 2CV, 30 to 50 over 4CV, 50 for 6CV)

Sources & evidence

ORD record: ord-3d1ee3cea7c7498f849168588d5b14d3
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266876B2

Reaction notes

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