Hydrochloric Acid → HCID 9834916, compound

HRID 1582459Notes

Reaction equation

HRID 1582459 reaction equation
[N+:1](/[CH:4]=[CH:5]/[C:6]1[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:8]2[CH2:15][CH2:16][N:17](C(OC(C)(C)C)=O)[CH2:18][CH2:19][C:7]=12)([O-:3])=[O:2].Cl>CO>[N+:1](/[CH:4]=[CH:5]/[C:6]1[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:8]2[CH2:15][CH2:16][NH:17][CH2:18][CH2:19][C:7]=12)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22720618HCID 22720618, compound

Product 1

HCID 9834916HCID 9834916, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of tert-butyl 11-[(E)-2-nitroethenyl]-1,2,4,5-tetrahydro-3H-[1,4]diazepino[1,7-a]indole-3-carboxylate (396 mg, 1.1 mmol) in methanol (10 mL) is cooled to 0° C. and treated with a saturated solution of hydrochloric acid in methanol (5 mL). After 3 hrs, the volatiles are removed under reduced pressure, diluted with 5M sodium hydroxide (15 mL), and extracted twice with dichloromethane (20 mL). The combined organics are washed once with brine (15 mL), dried over MgSO4, filtered, and concentrated to give a yellow solid. This material is recrystallized from dichloromethane/ethyl acetate to afford 209 mg of 11-[(E)-2-nitroethenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole as a light yellow solid, mp 225-226° C. IR (drift) 1603, 1488, 1469, 1318, 1301, 1281, 1257, 1251, 1206, 1187, 1062, 976, 946, 763, 745 cm−1; OAMS supporting ions at: ESI+ 258.1.

Workup

  1. customthe volatiles are removed under reduced pressure
  2. additiondiluted with 5M sodium hydroxide (15 mL)
  3. extractionextracted twice with dichloromethane (20 mL)
  4. washThe combined organics are washed once with brine (15 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a yellow solid
  9. customThis material is recrystallized from dichloromethane/ethyl acetate

Sources & evidence

ORD record
ord-20b3ad675ffe462da4204a4077bd4509
Source dataset
uspto-grants-2004_05
Patent number
US06734301B2

Reaction notes

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