4-Nitrophthalic acid anhydride → HCID 21400824, compound

HRID 973105Notes

Reaction equation

HRID 973105 reaction equation
[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[C:6]1[CH3:14])[CH2:2][CH2:3][CH3:4].[N+:15]([C:18]1[CH:19]=[C:20]2[C:25](=[O:26])[O:24][C:22](=[O:23])[C:21]2=[CH:27][CH:28]=1)([O-:17])=[O:16]>C(OC(=O)C)C>[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:22](=[O:23])[C:21]2[CH:27]=[CH:28][C:18]([N+:15]([O-:17])=[O:16])=[CH:19][C:20]=2[C:25]([OH:26])=[O:24])=[C:6]1[CH3:14])[CH2:2][CH2:3][CH3:4].[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:25](=[O:26])[C:20]2[CH:19]=[C:18]([N+:15]([O-:17])=[O:16])[CH:28]=[CH:27][C:21]=2[C:22]([OH:24])=[O:23])=[C:6]1[CH3:14])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 2309764-Nitrophthalic acid anhydrideHCID 30848831H-Indole, 1-butyl-2-methyl-

Product 2

HCID 21400824HCID 21400824, compoundHCID 21400825HCID 21400825, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 12.35 g of 1n-butyl-2-methylindole in 20 ml ethylacetate at 70° C, 11.6 g 4-nitrophthalic anhydride is added over 10 minutes. The reaction mixture is stirred under reflux at 80° C for C. hour and cooled to 20° C The crystalline solid thus obtained is filtered off, washed with a mixture of ethyl acetate and petroleum ether and dried in vacuo at 80° C to yield 19.6 g (86% of theory) of the two isomers 1-n-butyl-2-methyl-3-(2'-carboxy-4'-nitrobenzoyl) indole and 1-n-butyl-2-methyl-3-(2'-carboxy-5'-nitro-benzoyl)-indole having a melting point of 165°-167° C.

Workup

  1. temperaturehour and cooled to 20° C The crystalline solid
  2. customthus obtained
  3. filtrationis filtered off
  4. washwashed with a mixture of ethyl acetate and petroleum ether
  5. customdried in vacuo at 80° C

Sources & evidence

ORD record
ord-76b6206f2cc944629857a6330207ef07
Source dataset
uspto-grants-1977_10
Patent number
US04055358

Reaction notes

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