Sulfuric Acid → HCID 54374617, compound

HRID 36624

Reaction equation

HRID 36624 reaction equation
[CH:1]1[CH:10]=[C:9]2[C:11]([O:13][C:14](=[O:15])[C:7]3=[C:8]2[C:3](=[C:4]([NH2:16])[CH:5]=[CH:6]3)[CH:2]=1)=[O:12].S(=O)(=O)(O)O.[N+](C1C=CC=CC=1)([O-])=O.[CH3:31][C:32]([CH:34](OC(C)=O)OC(C)=O)=[CH2:33]>C(O)(=O)C.O>[CH3:34][C:32]1[CH:33]=[C:5]2[C:4]([C:3]3[CH:2]=[CH:1][CH:10]=[C:9]4[C:11](=[O:12])[O:13][C:14](=[O:15])[C:7](=[CH:6]2)[C:8]=34)=[N:16][CH:31]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 7416NitrobenzeneHCID 25305Methacrolein diacetateHCID 809904-Aminonaphthalene-1,8-dicarboxylic anhydride

Product 1

HCID 54374617HCID 54374617, compoundYield 93.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 4-amino-1,8-naphthalic anhydride (Okazaki, M.; Ishikawa, N. Yuki Gosei Kagaku Kyokai Shi 1956, 14, 398; Chem. Abstr. 1957, 51, 8051c) (28.0 g, 131 mmol), ferrous sulfate heptahydrate (7.20 g, 25.8 mmol), concentrated sulfuric acid (13 mL, 234 mmol), and nitrobenzene (27.0 mL, 262 mmol) in acetic acid (260 mL) was heated to reflux. Methallylidene diacetate (43.5 mL, 262 mmol) was added dropwise over a period of 2.5 h using an addition funnel. After the addition was complete, the reaction mixture was heated for 1.5 h and poured into a beaker of ice/water (500 mL). The aqueous solution was further diluted to 800 mL with water, stirred for 1 h and filtered by suction. The residue was washed with water and dried in vacuo to obtain 32.3 g of a dark brown solid. The crude solid was heated at reflux in acetic acid (80 mL) and filtered hot to obtain 15.63 g (44%) of a light brown solid: mp >290° C.; MS m/e 264 (M+H+); 1H NMR (DMSO-d6, 300 MHz) δ 2.60 (s, 3H), 8.10 (t, 1H), 8.60 (s, 1H), 8.62 (s, 1H), 9.01 (s, 1H), 9.12 (d, 1H), 9.45 (d, 1H).

Workup

  1. temperaturewas heated to reflux
  2. additionAfter the addition
  3. temperaturethe reaction mixture was heated for 1.5 h
  4. filtrationfiltered by suction
  5. washThe residue was washed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-e9d95a6fa62b41938daac5f7d4782911
Source dataset
uspto-grants-1995_05
Patent number
US05416089

Linked notes

Loading…