Hydrochloric Acid → HCID 10564705, compound

HRID 2292812Notes

Reaction equation

HRID 2292812 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-1efbdc65891d4dc3a6fddfc22e41ba91
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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