Hydrochloric Acid → HCID 18794842, compound

HRID 362290Notes

Reaction equation

HRID 362290 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22](OC)=[O:23])=[CH:17][CH:16]=1)[CH3:11].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>C(OCC)C.O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:12][CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][OH:23])=[CH:19][CH:20]=1)[CH3:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10382610HCID 10382610, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18794842HCID 18794842, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of methyl 2-[4-[2-[N-(2-benzoxazolyl)-N-methylamino]ethoxy]phenyl]ethanoate (11.60 g) in dry diethyl ether (200 mL) was added slowly to an ice-cooled, stirred suspension of lithium aluminium hydride (1.36 g) in ether (50 mL) under a nitrogen atmosphere. The mixture was stirred at 0° C. for 20 minutes, then water (10 mL) and hydrochloric acid (2M; 10 mL) were added dropwise with caution. The mixture was diluted with water (200 mL) was the solution adjusted to pH 4 prior to extraction with ethyl acetate (3×200 mL). The combined ethyl acetate solutions were washed with water (2×500 mL), brine (500 mL), dried (MgSO4) and evaporated to afford the title compound, mp 95°-97° C.

Workup

  1. temperaturecooled
  2. stirringThe mixture was stirred at 0° C. for 20 minutes
  3. extractionto extraction with ethyl acetate (3×200 mL)
  4. washThe combined ethyl acetate solutions were washed with water (2×500 mL), brine (500 mL)
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-477d90f9349344099e71fe348b6c73db
Source dataset
uspto-grants-1999_02
Patent number
US05869495

Reaction notes

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