Hydrochloric Acid → HCID 23458452, compound

HRID 903952Notes

Reaction equation

HRID 903952 reaction equation
[CH3:1][NH:2][C:3](=O)[CH:4]([OH:22])[CH:5]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14].B#B.CO.[ClH:28]>C1COCC1.C(OCC)C>[ClH:28].[CH3:1][NH:2][CH2:3][CH:4]([OH:22])[CH:5]([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 6328200Diboron2×HCID 15572612HCID 15572612, compound

Product 1

HCID 23458452HCID 23458452, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

50.3 g of N-methyl-2-hydroxy-3-phenyl-3-(2-nitro-phenoxy)-propionamide dissolved in 1000 ml of anhydrous THF was reduced to amine by slowly adding at 8° C. 340 ml of a molar solution of diborane in THF. The whole was refluxed for 4 hours, cooled to room temperature, the excess of diborane was decomposed with MeOH and then, again at room temperature, dropwise addition was made of 400 ml of an ethereal solution of HCl. The whole was left to stand for 16 hours and then evaporated to dryness at reduced pressure, taken up with CH2Cl2 and washed once with an aqueous solution of sodium bicarbonate. The organic phase was then washed several times with a saturated aqueous solution of NaCl, dried with sodium sulphate and evaporated to dryness. The dark oil forming the residue was dissolved in 800 ml of ethyl ether and alcoholic hydrochloric acid (18% solution in ETOH) was added; there was obtained 50.9 g of N-methyl-2-hydroxy-3-(2-nitro-phenoxy)-3-phenyl-propylamine. hydrochloride, m.p. 197°-203° C. (yield 94%).

Workup

  1. additionby slowly adding at 8° C
  2. temperatureThe whole was refluxed for 4 hours
  3. additionagain at room temperature, dropwise addition
  4. waitThe whole was left
  5. customevaporated to dryness at reduced pressure
  6. washwashed once with an aqueous solution of sodium bicarbonate
  7. washThe organic phase was then washed several times with a saturated aqueous solution of NaCl
  8. dry with materialdried with sodium sulphate
  9. customevaporated to dryness
  10. customThe dark oil forming the residue

Sources & evidence

ORD record
ord-b44366641d5f4ef2815ea95ca53c442f
Source dataset
uspto-grants-1980_10
Patent number
US04229449

Reaction notes

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