Formaldehyde → HCID 67243541, compound

HRID 2423129Notes

Reaction equation

HRID 2423129 reaction equation
[CH2:1]=O.[CH3:3][NH:4][CH2:5][CH2:6][OH:7].[CH3:8][C:9]1[CH:10]=[C:11]([OH:18])[CH:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[CH:14]2>CCO.C(Cl)Cl>[OH:7][CH2:6][CH2:5][N:4]([CH2:1][C:12]1[C:11]([OH:18])=[CH:10][C:9]([CH3:8])=[C:17]2[C:13]=1[CH:14]=[CH:15][NH:16]2)[CH3:3]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 80162-(Methylamino)ethanolHCID 189327347-methyl-1H-indol-5-ol2×

Product 1

HCID 67243541HCID 67243541, compoundYield 77.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of paraformaldehyde (82.0 mg, 2.71 mmol) and 2-methylaminoethanol (0.218 mL, 2.71 mmol) in EtOH (2 mL) was heated at 50° C. for 20 minutes. 7-methyl-1H-indol-5-ol (Intermediate 11, 500 mg, 3.4 mmol) in EtOH (10 mL) was added and the mixture was stirred for 1.5 hours at room temperature. The mixture was diluted with DCM (15 mL) and divided in two portions to be purified on two SCX-columns (5 g) preconditioned with DCM/MeOH 1:1 (20 mL) and eluted with DCM/MeOH 1:1 (50 mL) (contains only sm) and 1 M MeOH (40 mL) (contains product) to give 490 mg of a brown oil that turned solid. MS m/z 235 [M+H]+.

Workup

  1. customto be purified on two SCX-columns (5 g)
  2. washeluted with DCM/MeOH 1:1 (50 mL) (

Sources & evidence

ORD record
ord-12e19439141445c88474aa8166c3d198
Source dataset
uspto-grants-2011_06
Patent number
US07960374B2

Reaction notes

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