Dimethylformamide → HCID 19870558, compound

HRID 330159Notes

Reaction equation

HRID 330159 reaction equation
P(Cl)(Cl)(Cl)=O.[CH:6]([C:8]1[CH:16]=[C:15]2[C:11]([CH:12]=[CH:13][NH:14]2)=[CH:10][CH:9]=1)=[O:7].CN(C)[CH:19]=[O:20]>>[CH:19]([C:12]1[C:11]2[C:15](=[CH:16][C:8]([CH:6]=[O:7])=[CH:9][CH:10]=2)[NH:14][CH:13]=1)=[O:20]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 27734351H-Indole-6-carboxaldehyde

Product 1

HCID 19870558HCID 19870558, compoundYield 87%

Procedure

Phosphorous oxychloride (48.2 ml) was added dropwise to stirred N,N-dimethylformamide (72.8 ml) at 0° (internal temperature). Stirring was continued for about 1 hour, and a solution of 6-formylindole (32.7 g) (see Example 12, part b) in N,N-dimethylformamide (444 ml) was added dropwise, while maintaining the internal temperature at 0°. The cooling bath was removed and the mixture stirred for 18 hours before water (1 liter) was added and the mixture heated under reflux for 15 min. The mixture was cooled in an ice bath; and the precipitated product isolated by filtration, washed with water and dried under vacuum to give 3,6-diformylindole (33.97 g, 87%); mp 200°-203°; NMR (250 MHz, DMSO-d6): 7.75(dd, J=8.25, 1.25 Hz, 1H, H5 -indole), 8.10(s, 1H, H2 -indole), 8.24(d, J=8.25 Hz, 1H, H4 -indole), 8.57(s, 1H, H7 -indole), 10.00(s, 1H, CHO), 10.06(s, 1H, CHO); 12.61(br s, 1H, NH).

Workup

  1. temperaturewhile maintaining the internal temperature at 0°
  2. customThe cooling bath was removed
  3. stirringthe mixture stirred for 18 hours before water (1 liter)
  4. additionwas added
  5. temperaturethe mixture heated
  6. temperatureunder reflux for 15 min
  7. temperatureThe mixture was cooled in an ice bath
  8. customand the precipitated product isolated by filtration
  9. washwashed with water
  10. customdried under vacuum

Sources & evidence

ORD record
ord-be77c71c21ff4309b4bfbcca94b5c579
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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