Hydrochloric Acid → HCID 20523571, compound

HRID 1703227Notes

Reaction equation

HRID 1703227 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[N:5]([CH3:7])[CH3:6].[CH2:11]([N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([C:22]([C:24]2[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=2[C:26]([OH:28])=[O:27])=O)=[C:14]1[CH3:33])[CH3:12].Cl.[OH-].[Na+].[C:37](OC(=O)C)(=[O:39])[CH3:38]>>[C:37]([NH:1][C:2]1[CH:3]=[C:4]([N:5]([CH3:7])[CH3:6])[CH:8]=[CH:9][C:10]=1[C:22]1([C:15]2[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:13]([CH2:11][CH3:12])[C:14]=2[CH3:33])[C:24]2[C:25](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:26](=[O:28])[O:27]1)(=[O:39])[CH3:38]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 76084N,N-dimethyl-m-phenylenediamineHCID 3084978Benzoic acid, 2-[(1-ethyl-2-methyl-1H-indol-3-yl)carbonyl]-

Product 1

HCID 20523571HCID 20523571, compound

Procedure

A suspension of 1.36 g (0.01 mole) of m-amino-N,N-dimethylaniline in 20 ml of acetic anhydride was heated to 80°-90° C. for approximately thirty minutes and then cooled to room temperature. Three grams (0.01 mole) of 2-[(1-ethyl-2-methyl-3-indolyl)carbonyl]benzoic acid, prepared as described in part A of Example 1, was added and the resulting mixture was heated at 60°-70° C. for approximately thirty minutes. After cooling, the reaction mixture was poured into 100 ml of 10 percent hydrochloric acid and the mixture made alkaline with 10 percent aqueous sodium hydroxide with the addition of ice. The solid which separated was collected by filtration and dried to obtain 3-[2-acetamido-4-dimethylaminophenyl]-3-(1-ethyl-2-methyl-3-indolyl)phthalide (Formula III: R0 =R1 =R2 =R3 =Y1 =H; ##STR30## R=R5 =CH3 ; R6 =CH2CH3) as a pale blue-colored solid melting over the range 180°-195° C. Infrared absorption maxima appeared at 1757 cm-1 (C=O; s) and 1696 cm-1 (C=O; s).

Workup

  1. temperaturewas heated to 80°-90° C. for approximately thirty minutes
  2. additionwas added
  3. temperaturethe resulting mixture was heated at 60°-70° C. for approximately thirty minutes
  4. temperatureAfter cooling
  5. additionwith the addition of ice
  6. customThe solid which separated
  7. filtrationwas collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-219eea4de46c40daa8c8e57f00904d3a
Source dataset
uspto-grants-1982_09
Patent number
US04351768

Reaction notes

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