Hydrochloric Acid → HCID 15521876, compound

HRID 1066029Notes

Reaction equation

HRID 1066029 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=O.[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.Cl>CN(C)C=O>[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)=[O:7]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2280713-amino-4-nitrobenzoic acid

Product 1

HCID 15521876HCID 15521876, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In N,N-dimethylformamide (DMF) (108 ml), 3-amino-4-nitrobenzoic acid [the compound of the formula (1a)] (10.8 g) which was prepared in accordance with a known method (HECHENG HUASUE, page 91, 1995) was dissolved. Further, morpholine (10.3 ml), 1-Hydroxybenzotriazole (HOBt) (9.60 g), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (WSCI.HCl) (13.6 g) were successively added to the solution, and the mixture was stirred at room temperature for 18 hours. The reaction solution was poured into a 1N HCl aqueous solution to precipitate crystals, and the whole was filtrated to obtain the crystals and a filtrate. The filtrate was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The above crystals and the concentrate were combined to obtain 3-amino-4-nitrobenzoic acid morpholide (12.1 g; yield=81.2%) as yellow crystals.

Workup

  1. dissolutionwas dissolved
  2. customto precipitate crystals
  3. filtrationthe whole was filtrated
  4. customto obtain the crystals
  5. extractionThe filtrate was extracted with ethyl acetate
  6. dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d20d73d267bd4f8181c964d4cc8ea0ad
Source dataset
uspto-grants-2001_06
Patent number
US06242445B1

Reaction notes

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