Pyridine → HCID 68675391, compound

HRID 2267122Notes

Reaction equation

HRID 2267122 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:4]=1[NH2:5].N1C=CC=CC=1.[C:19](Cl)([O:21][CH2:22][CH:23]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]2[C:24]1=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:20]>C1COCC1>[C:19]([C:4]1([CH:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][CH:3]1[O:2][CH3:1])[NH2:5])([O:21][CH2:22][CH:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:30]2[C:35]1=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 73372-Methoxy-4-nitroanilineHCID 343679-Fluorenylmethyl chloroformate

Product 1

HCID 68675391HCID 68675391, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-methoxy-4-nitroaniline (3.0 g) and pyridine (1.6 ml) in THF (30 ml) was cooled to 0° C. FmocCl (5.07 g) was added in portions and after complete addition the ice-bath was removed and the mixture was stirred for 5 h. The THF was removed in vacuo and the residue dissolved in CH2Cl2 (175 ml). Methanol (ca 100 ml) was added and the CH2Cl2 was partly removed in vacuo until a precipitate formed. The mixture was allowed to stand for 1 h, after which time the crystals were collected by filtration and dried in vacuo to give the title compound.

Workup

  1. customwas removed
  2. customThe THF was removed in vacuo
  3. dissolutionthe residue dissolved in CH2Cl2 (175 ml)
  4. additionMethanol (ca 100 ml) was added
  5. customthe CH2Cl2 was partly removed in vacuo until a precipitate
  6. customformed
  7. waitto stand for 1 h
  8. filtrationafter which time the crystals were collected by filtration
  9. customdried in vacuo

Sources & evidence

ORD record
ord-88718afbec82417e9c9ad9d42bedb5c6
Source dataset
uspto-grants-2010_12
Patent number
US07858794B2

Reaction notes

Loading…