Dimethylformamide → 1-Methyl-2,5-dichloroindole-3-carbaldehyde

HRID 1957199Notes

Reaction equation

HRID 1957199 reaction equation
O=P(Cl)(Cl)[Cl:3].[CH3:6][N:7]([CH:9]=O)[CH3:8].CN1C2[C:15](=[CH:16][C:17]([Cl:21])=[CH:18][CH:19]=2)[CH2:14][C:13]1=[O:22].C([O-])(O)=O.[Na+]>ClCCl.N1C=CC=CC=1>[CH3:8][N:7]1[C:6]2[C:15](=[CH:16][C:17]([Cl:21])=[CH:18][CH:19]=2)[C:14]([CH:13]=[O:22])=[C:9]1[Cl:3]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 109761125-chloro-1-methyl-2,3-dihydro-1H-indol-2-one

Product 1

HCID 190689371-Methyl-2,5-dichloroindole-3-carbaldehyde

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

POCl3 (6 ml) was added dropwise to a mixture of dry DMF (5.9 ml) and dichloromethane (5.9 ml) kept at 0° C. 1-Methyl-5-chloro-1,3-dihydroindol-2-one (4.0 g) dissolved in dichloromethane (20 ml) and pyridine (2.9 ml) was added dropwise at 0° C. over a period of 30 min. Subsequent stirring at room temperature for 3h. The mixture was poured onto icewater (500 ml) neutralized with NaHCO3 whereafter the mixture was stirred overnight. The precipitate was filtered off, washed with water and dried. The crude material (4.45 g) was recrystallized from ethanol yielding 1.27 g (25.4%) of (45). M.p. 165°-167° C.

Workup

  1. customkept at 0° C
  2. additionThe mixture was poured onto icewater (500 ml)
  3. stirringwas stirred overnight
  4. filtrationThe precipitate was filtered off
  5. washwashed with water
  6. customdried
  7. customThe crude material (4.45 g) was recrystallized from ethanol yielding 1.27 g (25.4%) of (45)

Sources & evidence

ORD record
ord-8e1f83e0ed46484696b0288782d34c31
Source dataset
uspto-grants-1998_07
Patent number
US05783575

Reaction notes

Loading…