Triphenylphosphine → HCID 12988784, compound

HRID 395331Notes

Reaction equation

HRID 395331 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][C:17]=1[N+:23]([O-:25])=[O:24].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[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:22][C:19]2[CH:20]=[CH:21][C:16]([NH2:15])=[C:17]([N+:23]([O-:25])=[O:24])[CH:18]=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 37588824-Amino-3-Nitrophenol

Product 1

HCID 12988784HCID 12988784, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropyl azodicarboxylate (1.1 eq) was added dropwise to a stirred solution of 4-amino-3-nitrophenol (1.0 eq), triphenylphosphine (1.1 eq), and an alcohol, e.g. N-(2-hydroxyethyl)morpholine (1.0 eq), 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+), Rf 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+), Rf 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-bb8e1619e65f42269f5b93843e08b580
Source dataset
uspto-grants-2003_08
Patent number
US06605617B2

Reaction notes

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