Hydrochloric Acid → HCID 10564705, compound

HRID 1069649Notes

Reaction equation

HRID 1069649 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:7]=[C:6]2[CH2:19][C:20]([NH2:22])=[O:21].B(Br)(Br)Br.C(Cl)Cl.Cl>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:7]=[C:6]2[CH2:19][C:20]([NH2:22])=[O:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10732550HCID 10732550, compoundHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 10564705HCID 10564705, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 375 mg (1.23 mmol) of 5-methoxy-1-(phenylmethyl)-1H-indole-3-acetamide (Example 3) and 5 mL of 1M BBr3/methylene chloride in 75 mL of methylene chloride was stirred for 1.25 hours, and poured into 1N HCl. The methylene chloride layer was separated, washed with brine and dried (Na2SO4). The solvent was removed at reduced pressure to give as residue 310 mg (90% yield) of 5-hydroxy-1-(phenylmethyl)-1H-indole-3-acetamide, mp, 158-160° C.

Workup

  1. customThe methylene chloride layer was separated
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. customThe solvent was removed at reduced pressure

Sources & evidence

ORD record
ord-7d26c37d4a0541789d959939aa2ab72b
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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