Water → HCID 12803112, compound

HRID 1904771Notes

Reaction equation

HRID 1904771 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[C:9]2[CH2:15][C:16]#[N:17].N1C=CC=CC=1.O>C(#N)C>[C:16]([CH2:15][C:9]1[C:8]2[C:12](=[CH:13][CH:14]=[C:6]([NH:5][C:1](=[O:3])[CH3:2])[CH:7]=2)[NH:11][CH:10]=1)#[N:17]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6367Acetyl chlorideHCID 12803100HCID 12803100, compound

Product 1

HCID 12803112HCID 12803112, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Acetyl chloride (0.21 ml) was added dropwise to a stirred solution of 5-amino-1H-indole-3-acetonitrile (0.5 g) and pyridine (0.24 ml) in dry acetonitrile (10 ml) at 0°-2° under nitrogen. When the addition was complete the solution was stirred at 0° for 30 minutes, poured into water (50 ml) and extracted with ethyl acetate (3×25 ml). The combined extracts were dried (MgSO4), filtered and evaporated under reduced pressure to a brown solid (0.5 g) which was crystallised from an ethanol-cyclohexane mixture to give the title compound (0.43 g) as off-white needles, m.p. 171.5°-175°.

Workup

  1. additionWhen the addition
  2. extractionextracted with ethyl acetate (3×25 ml)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure to a brown solid (0.5 g) which
  6. customwas crystallised from an ethanol-cyclohexane mixture

Sources & evidence

ORD record
ord-7a858b70e008480b8bb53a3d4f5daf06
Source dataset
uspto-grants-1989_06
Patent number
US04839377

Reaction notes

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