Triphenylphosphine → HCID 12988784, compound

HRID 1169983Notes

Reaction equation

HRID 1169983 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[NH2:15][C:16]1[CH:17]=[C:18](O)[CH:19]=[CH:20][C:21]=1[N+:22]([O-:24])=[O:23].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:45][CH2:46][CH2:47][N:48]1[CH2:53][CH2:52][O:51][CH2:50][CH2:49]1>O1CCCC1>[N:48]1([CH2:47][CH2:46][O:45][C:19]2[CH:18]=[CH:17][C:16]([NH2:15])=[C:21]([N+:22]([O-:24])=[O:23])[CH:20]=2)[CH2:53][CH2:52][O:51][CH2:50][CH2:49]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 611632-MorpholinoethanolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 1675273-Amino-4-nitrophenol

Product 1

HCID 12988784HCID 12988784, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropyl azodicarboxylate (1.1 equivalents) was added dropwise to a stirred solution of 3-amino-4-nitrophenol (1.0 equivalent), triphenylphosphine (1.1 equivalents), and an alcohol, e.g. N-(2-hydroxyethyl)morpholine (1.0 equivalent), in tetrahydrofuran at 0° C. The mixture was allowed to warm to room temperature and stirred for 18 hours. The solvent was evaporated, and the product was purified by silica gel chromatography (98:2 CH2Cl2:methanol) to yield 4-(2-morpholin-4-ylethoxy)-2-nitrophenylamine as a dark reddish-brown oil. LC/MS m/z 268.0 (MH+), Rt 1.01 minutes. The nitroamine was reduced as in Method 1 to give the crude product which was used without further purification. LC/MS m/z 238.3 (MH+), Rt 0.295 minutes.

Workup

  1. customat 0° C
  2. customThe solvent was evaporated
  3. customthe product was purified by silica gel chromatography (98:2 CH2Cl2:methanol)

Sources & evidence

ORD record
ord-376c7b91d3de46a3af9006f953cf13af
Source dataset
uspto-grants-2010_11
Patent number
US07825132B2

Reaction notes

Loading…