HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Hydrochloric Acid → [1-(4-methoxy-benzyl)-3-methyl-1H-indol-6-yl]-phenyl methanone

HRID 380407
Notes
Print preview

Reaction equation

HRID 380407 reaction equation
CON(C)[C:4]([C:6]1[CH:14]=[C:13]2[C:9]([C:10]([CH3:24])=[CH:11][N:12]2[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[CH:8][CH:7]=1)=[O:5].[C:26]1([Mg]Cl)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.Cl>O1CCCC1>[CH3:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][N:12]2[C:13]3[C:9](=[CH:8][CH:7]=[C:6]([C:4]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[O:5])[CH:14]=3)[C:10]([CH3:24])=[CH:11]2)=[CH:17][CH:18]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 22663398N-methoxy-1-(4-methoxybenzyl)-3-methyl-N-methyl-1H-indole-6-carboxamideHCID 178478979HCID 178478979, compound

Product 1

HCID 22663420[1-(4-methoxy-benzyl)-3-methyl-1H-indol-6-yl]-phenyl methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A stirred solution of N-methoxy-1-(4-methoxybenzyl)-3-methyl-N-methyl-1H-indole-6-carboxamide (2.215 g, Example 25) in tetrahydrofuran (55 ml) was treated with a solution of phenylmagnesium chloride in tetrahydrofuran (9.83 ml, 2M). The solution was stirred at 0° C. for 2 hours then poured into a mixture of ice and 1N hydrochloric acid (10 ml) and then partitioned between ethyl acetate (50 ml) and water (50 ml). The organic layer was dried over sodium sulphate then evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and hexane (1:2, v/v) to yield the title compound (2.05 g) as a yellow solid, m.p. 146-147° C. [Elemental analysis:—C,80.80; H,6.00; N,3.80%. Calculated for C24H21NO2:—C,81.10; H,5.96; N,3.94%].

Workup

  1. custompartitioned between ethyl acetate (50 ml) and water (50 ml)
  2. dry with materialThe organic layer was dried over sodium sulphate
  3. customthen evaporated
  4. additionThe residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and hexane (1:2

Sources & evidence

ORD record
ord-8d5d43353a164b3b8ac7bf9b9a9f43aa
Source dataset
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06303600B1

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes