Acetic Anhydride → HCID 14149591, compound

HRID 648805Notes

Reaction equation

HRID 648805 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N:8]([CH2:11][CH3:12])[CH2:9][CH3:10])[CH:5]=[CH:4][C:3]=1[C:13]([C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([OH:19])=O)=[O:14].[CH:24]([O:26][CH2:27][CH2:28][N:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[C:30]1[CH3:38])=[CH2:25].C(OC(=O)C)(=O)C.[OH-].[NH4+]>C1(C)C=CC=CC=1>[CH:24]([O:26][CH2:27][CH2:28][N:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]([C:13]2([C:3]3[CH:4]=[CH:5][C:6]([N:8]([CH2:9][CH3:10])[CH2:11][CH3:12])=[CH:7][C:2]=3[CH3:1])[C:15]3[C:16](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:17](=[O:19])[O:14]2)=[C:30]1[CH3:38])=[CH2:25]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 14923Ammonium HydroxideHCID 1043352-(4-(Diethylamino)-2-methylbenzoyl)benzoic acidHCID 21283989HCID 21283989, compound

Product 1

HCID 14149591HCID 14149591, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 15.6 g of 2-(2-methyl-4-dietylaminophenyl)carbonylbenzoic acid, 12.5 g of 1-(2-vinyloxyethyl)-2-methylindole, and 50.0 ml of acetic anhydride was maintained at approximately 70° C. for approximately four hours. The resulting solution was cooled to ambient temperature and slowly poured into a mixture of toluene and 5 percent aqueous ammonium hydroxide. The toluene layer was separated, washed successively once each with water and saturated sodium chloride solution and evaporated to dryness. The residue that remained was heated in a 1:1 mixture of isopropyl alcohol:hexane. The liquid was decanted from a gummy residue. The residue was dissolved in 100.0 ml of acetone and the resulting solution was added dropwise to 1500.0 ml of 2 percent aqueous ammonium hydroxide. The solid which precipitated was collected by filtration, washed with water and dried to obtain 18.86 g of 3-[1-(2-vinyloxyethyl)-2-methylindol-3-yl]-3-(2-methyl-4-diethylaminophenyl)phthalide (Formula I: R1 =CH2 =CHOC2H4 ; R1 =R2 =CH3 ; R3 =R4 =C2H5 ; X=Y=H), a tan-colored solid which melted over the range 135°-141° C. Significant infrared maxima appeared at 1760 (C=O; s) and 1120 (C--O; s)cm-1. A toluene solution of the product spotted on an acid clay or a phenolic resin coated paper developed a cyan-colored image.

Workup

  1. temperatureThe resulting solution was cooled to ambient temperature
  2. customThe toluene layer was separated
  3. washwashed successively once each with water and saturated sodium chloride solution
  4. customevaporated to dryness
  5. temperatureThe residue that remained was heated in a 1:1 mixture of isopropyl alcohol
  6. customThe liquid was decanted from a gummy residue
  7. dissolutionThe residue was dissolved in 100.0 ml of acetone
  8. additionthe resulting solution was added dropwise to 1500.0 ml of 2 percent aqueous ammonium hydroxide
  9. customThe solid which precipitated
  10. filtrationwas collected by filtration
  11. washwashed with water
  12. customdried

Sources & evidence

ORD record
ord-72c9beb012274b2a887903a72c6c2202
Source dataset
uspto-grants-1988_04
Patent number
US04736027

Reaction notes

Loading…