HCID 21276193, compound → HCID 14391137, compound

HRID 1381556Notes

Reaction equation

HRID 1381556 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([NH2:11])=[CH:8][CH:9]=2)[C:4]([CH2:12][C:13]#[N:14])=[CH:3]1.[O:15]([C:17]#[N:18])[K]>>[C:13]([CH2:12][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([NH:11][C:17]([NH2:18])=[O:15])[CH:6]=2)[N:2]([CH3:1])[CH:3]=1)#[N:14]

Participants

3

Reactant 2

HCID 21276193HCID 21276193, compoundHCID 178418250HCID 178418250, compound

Product 1

HCID 14391137HCID 14391137, compoundYield 80%

Procedure

A solution of 7.0 g (0.038 mole) of 1-methyl-5-aminoindole-3-acetonitrile was treated with KOCN as in Example 1 to give a beige solid which was filtered off, washed with cold water and triturated with 50% aq. EtOH to give 6.95 g (80%) of a beige solid: m.p. 250° (dec); nmr (d6 -DMSO) δ(TMS) 8.41 (1, s), 7.65 (1, s), 7.42-7.08 (3, m), 5.73 (2, s, --NH2 --), 4.00 (2, s, --CH2 --) and 3.73 ppm (3H, S, N--CH3).

Workup

  1. customto give a beige solid which
  2. filtrationwas filtered off
  3. washwashed with cold water
  4. customtriturated with 50% aq. EtOH

Sources & evidence

ORD record
ord-f6c6bba17d1a4f7e94216cb403679c76
Source dataset
uspto-grants-1989_02
Patent number
US04803218

Reaction notes

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