Sulfuric Acid → HCID 19711229, compound

HRID 724870Notes

Reaction equation

HRID 724870 reaction equation
S(=O)(=O)(O)O.[NH2:6][C:7]1[C:12]2[O:13][CH2:14][CH2:15][O:16][C:11]=2[C:10]([C:17]([O:19][CH3:20])=[O:18])=[CH:9][CH:8]=1.[N+:21]([O-])([O-:23])=[O:22].[K+].C(=O)([O-])[O-].[K+].[K+]>O.C(O)(=O)C>[NH2:6][C:7]1[C:12]2[O:13][CH2:14][CH2:15][O:16][C:11]=2[C:10]([C:17]([O:19][CH3:20])=[O:18])=[CH:9][C:8]=1[N+:21]([O-:23])=[O:22]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 24434Potassium NitrateHCID 19711232Methyl 8-amino-2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylate

Product 1

HCID 19711229HCID 19711229, compoundYield 16.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Concentrated sulphuric acid (6.5 ml) was treated cautiously with stirring at 5°-10° C. with glacial acetic acid (12 ml) and to the resulting solution was added methyl 8-amino-1,4-benzodioxan-5-carboxylate (1.5 g, 0.0072 mole). The mixture was stirred at room temperature for 1 h, then treated portionwise over 45 minutes with potassium nitrate (0.85 g, 0.0084 mole). The mixture was stirred for a further 4 h then poured into water (100 ml) and basified with potassium carbonate. A precipitate was produced and this was filtered off, washed with water and dried to afford methyl 8-amino-7-nitro-1,4-benzodioxan-5-carboxylate as a yellow solid (0.30 g). The filtrate was extracted with ethyl acetate and the extract dried (Na2SO4) and concentrated in vacuo to afford a further 1.1 g of the product as an orange solid. 1H NMR (CDCl3) δ:8.50(s,1 H), 6.0-7.0(v br,2 H), 4.30-4.55(m,4 H), 3.87(s,3 H).

Workup

  1. stirringThe mixture was stirred for a further 4 h
  2. customA precipitate was produced
  3. filtrationthis was filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-58e524ce1d3c401295c5651fdbbb0669
Source dataset
uspto-grants-1998_01
Patent number
US05705509

Reaction notes

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