Hydrochloric Acid → HCID 22839557, compound

HRID 622077Notes

Reaction equation

HRID 622077 reaction equation
[F:1][C:2]1[C:7]2[CH2:8][C@H:9]3[CH2:13][N:12](CC4C=CC=CC=4)[CH2:11][C@@H:10]3[O:21][C:6]=2[CH:5]=[CH:4][CH:3]=1.[ClH:22]>CO>[ClH:22].[F:1][C:2]1[C:7]2[CH2:8][C@H:9]3[CH2:13][NH:12][CH2:11][C@@H:10]3[O:21][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22839558HCID 22839558, compound

Product 1

HCID 22839557HCID 22839557, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of Example 1 (0.42 g) in methanol (10 mls) was treated with excess hydrogen chloride in methanol and the solution was evaporated to dryness. The residue was redissolved in methanol and was hydrogenated over 10% palladium on charcoal (50 mg) at 40°-50° until reaction was complete. The solvent was evaporated, the product was treated with hydrogen chloride in ethanol, evaporated to dryness and the solid was triturated with isopropyl alcohol to give the title compound (0.25 g). M.p. 220°-2°. NMR (DMSOd6) δ 9.72 (2H, Br-s, NH2+), 7.22 (1H, q, 6-H), 6.9-6.7 (2H, m, 5-H, 7-H), 4.21 (1H, d of t, 3a-H), 3.78-2.6 (6H, m, 3-H2, 1-H2, 9-H2), 2.22 (1H, m, 9a-H).

Workup

  1. customthe solution was evaporated to dryness
  2. dissolutionThe residue was redissolved in methanol
  3. customwas hydrogenated over 10% palladium on charcoal (50 mg) at 40°-50° until reaction
  4. customThe solvent was evaporated
  5. additionthe product was treated with hydrogen chloride in ethanol
  6. customevaporated to dryness
  7. customthe solid was triturated with isopropyl alcohol

Sources & evidence

ORD record
ord-47d67d0f02c946678fb5641faacb0ecd
Source dataset
uspto-grants-1988_09
Patent number
US04769367

Reaction notes

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