Acetic Anhydride → HCID 20300069, compound

HRID 1733556Notes

Reaction equation

HRID 1733556 reaction equation
[CH2:1]([N:3]([CH2:28][CH3:29])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:12]2[C:21]([C:22]([OH:24])=O)=[N:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)=[O:11])=[C:6]([O:25][CH2:26][CH3:27])[CH:5]=1)[CH3:2].[CH3:30][C:31]1[C:32]2[N:33]([CH:37]=[C:38]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[N:39]=2)[CH:34]=[CH:35][CH:36]=1.C(OC(=O)C)(=O)C>C1(C)C=CC=CC=1>[CH2:1]([N:3]([CH2:28][CH3:29])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:37]3[N:33]4[CH:34]=[CH:35][CH:36]=[C:31]([CH3:30])[C:32]4=[N:39][C:38]=3[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:12]3[C:21](=[N:20][C:19]4[C:14]([N:13]=3)=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:22](=[O:24])[O:11]2)=[C:6]([O:25][CH2:26][CH3:27])[CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 6596428-methyl-2-phenylimidazo[1,2-a]pyridineHCID 20300074HCID 20300074, compound

Product 1

HCID 20300069HCID 20300069, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3.9 grams of (4-diethylamino-2-ethoxyphenyl)(3-carboxyquinoxalin-2-yl)ketone, 2.1 grams of 8-methyl-2-phenylimidazo[1,2-a]pyridine and 15 ml. of acetic anhydride was heated at 80° C. for 1 hour and poured into a mixture of ice ammonia and toluene. The toluene portion was separated, washed with saturated sodium sulfate solution, filtered through phase separation paper and concentrated. Petroleum ether was added to the concentrate and 2.7 grams of crystalline material was filtered off. This material was recrystallized four times from a mixture of toluene and petroleum ether to yield a final product with a melting point of 135°-136° C. A solution of the product produced a blue color when applied to a record sheet material coated with a zinc-modified phenolic resin or silton clay.

Workup

  1. customThe toluene portion was separated
  2. washwashed with saturated sodium sulfate solution
  3. filtrationfiltered through phase separation paper
  4. concentrationconcentrated
  5. additionPetroleum ether was added to the
  6. concentrationconcentrate
  7. filtration2.7 grams of crystalline material was filtered off
  8. customThis material was recrystallized four times
  9. additionfrom a mixture of toluene and petroleum ether

Sources & evidence

ORD record
ord-44206cf49e5f489dbb9ea60236342c02
Source dataset
uspto-grants-1980_12
Patent number
US04242513

Reaction notes

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