2-Methylindole → HCID 21400823, compound

HRID 973104Notes

Reaction equation

HRID 973104 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[C:6]2[C:7]([O:9][C:10](=[O:11])[C:5]=12)=[O:8])([O-:3])=[O:2].[CH3:15][C:16]1[NH:17][C:18]2[C:23]([CH:24]=1)=[CH:22][CH:21]=[CH:20][CH:19]=2>C1(C)C=CC=CC=1>[C:10]([C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:14][CH:13]=[CH:12][C:6]=1[C:7]([C:24]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][C:16]=1[CH3:15])=[O:8])([OH:9])=[O:11].[C:7]([C:6]1[CH:12]=[CH:13][CH:14]=[C:4]([N+:1]([O-:3])=[O:2])[C:5]=1[C:10]([C:24]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][C:16]=1[CH3:15])=[O:11])([OH:9])=[O:8]

Participants

5

Reactant 2

HCID 72242-MethylindoleHCID 216313-Nitrophthalic anhydride

Product 2

HCID 21400823HCID 21400823, compoundHCID 21400826HCID 21400826, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 19,3 g 3-nitrophthalic anhydride, 13,1 g 2-methylindole and 60 ml toluene is heated for 3 hours at 100° C and cooled to 25° C. The precipitate thus obtained is filtered off, washed with toluene and methanol and dried in vacuo 80° C to yield 25,9 g (80% of theory) of the two isomers 3-(2'-carboxy-3'-nitro-benzoyl)-2-methyl indole and 3-(2'-carboxy-6'-nitro-benzoyl)-2-methyl indole, having a melting point of 199° - 202° C.

Workup

  1. temperaturecooled to 25° C
  2. customThe precipitate thus obtained
  3. filtrationis filtered off
  4. washwashed with toluene and methanol
  5. customdried in vacuo 80° C

Sources & evidence

ORD record
ord-c78782b70544410b9ca8ff8d9bd225ae
Source dataset
uspto-grants-1977_10
Patent number
US04055358

Reaction notes

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