Ammonia → HCID 57095491, compound

HRID 1863526Notes

Reaction equation

HRID 1863526 reaction equation
[CH2:1]([N:3]([CH2:43][CH3:44])[C:4]1[CH:9]=[CH:8][C:7]2[C:10]3([C:20]4[CH:21]=[C:22]5[C:27](=[CH:28][C:29]=4[O:30][C:6]=2[CH:5]=1)[N:26]=[C:25]([CH:31]=CC1C=CC(N(C)C)=CC=1)[CH:24]=[C:23]5[CH3:42])[C:18]1[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:12](=[O:19])[O:11]3)[CH3:2].[N+:45]([C:48]1[CH:55]=[CH:54][C:51]([CH:52]=O)=[CH:50][CH:49]=1)([O-:47])=[O:46].C(OC(=O)C)(=O)C.N>O>[CH2:43]([N:3]([CH2:1][CH3:2])[C:4]1[CH:9]=[CH:8][C:7]2[C:10]3([C:20]4[CH:21]=[C:22]5[C:27](=[CH:28][C:29]=4[O:30][C:6]=2[CH:5]=1)[N:26]=[C:25]([CH:31]=[CH:52][C:51]1[CH:54]=[CH:55][C:48]([N+:45]([O-:47])=[O:46])=[CH:49][CH:50]=1)[CH:24]=[C:23]5[CH3:42])[C:18]1[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:12](=[O:19])[O:11]3)[CH3:44]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 5414-NitrobenzaldehydeHCID 7918Acetic AnhydrideHCID 57312628HCID 57312628, compound

Product 1

HCID 57095491HCID 57095491, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

2.3 grams (0.005 moles) of 9-(diethylamino)-2-(4-dimethylaminostyryl)-4-methylspiro [6H-[1] benzopyrano [3,2-g] quinoline-6,1'(3'H)-isobenzofuran]-3'-one, 0.6 grams (0.005 moles) of p-nitrobenzaldehyde and 0.5 grams (0.005 moles) of acetic anhydride were mixed in a flask fitted with a reflux condensor, then heated in an oil bath at 160° C. for 4 hours. The bath was cooled and 50 ml of water was added. The mixture was then made alkaline with ammonia, extracted with 100 ml of toluene, dried over sodium sulfate, treated with activated charcoal (DARCO) and filtered. The volume of the solution was reduced to 25 ml by evaporation of the toluene. Ligroine was added to precipitate the product. The yellow-orange solids were filtered off and dried to yield 1.5 grams of product. The reaction sequence was as follows: ##STR15##

Workup

  1. customfitted with a reflux condensor
  2. temperatureThe bath was cooled
  3. extractionextracted with 100 ml of toluene
  4. dry with materialdried over sodium sulfate
  5. additiontreated with activated charcoal (DARCO)
  6. filtrationfiltered
  7. customThe volume of the solution was reduced to 25 ml by evaporation of the toluene
  8. additionLigroine was added
  9. customto precipitate the product
  10. filtrationThe yellow-orange solids were filtered off
  11. customdried

Sources & evidence

ORD record
ord-023991a9163a4caea3ca7324286d752d
Source dataset
uspto-grants-1979_09
Patent number
US04169183

Reaction notes

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