2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 20337305, compound

HRID 1706135Notes

Reaction equation

HRID 1706135 reaction equation
[BrH:1].[OH:2][C:3]1[C:19]([OH:20])=[CH:18][C:6]2[CH:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:8][NH:9][CH2:10][CH2:11][C:5]=2[CH:4]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>CO>[BrH:1].[C:12]1([CH:7]2[C:6]3=[CH:18][C:19](=[O:20])[C:3](=[O:2])[CH:4]=[C:5]3[CH2:11][CH2:10][NH:9][CH2:8]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 12928470SKF-38393 (hydrobromide)

Product 1

HCID 20337305HCID 20337305, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a suspension of 7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrobromide (34 g, 0.101 mole, U.S. Pat. No. 3,393,192) in methanol (275 ml) was added a solution of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (25.2 g, 0.111 mole) in methanol (125 ml). The addition was carried out rapidly with stirring at 0° under an argon atmosphere. After stirring at 0° for 1 hour the reaction mixture was filtered and the orange precipitate was washed with cold methanol (75 ml), ethyl acetate (100 ml) and then diethyl ether (100 ml). After drying at room temperature under vacuum, 1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-dione hydrobromide (32.8 g, 0.98 mole, 97%) was obtained, mp 164°-165° (dec.).

Workup

  1. additionThe addition
  2. stirringAfter stirring at 0° for 1 hour the reaction mixture
  3. filtrationwas filtered
  4. washthe orange precipitate was washed with cold methanol (75 ml), ethyl acetate (100 ml)
  5. customAfter drying at room temperature under vacuum

Sources & evidence

ORD record
ord-fc4ea691aef94857966275080c3aa70e
Source dataset
uspto-grants-1980_06
Patent number
US04206210

Reaction notes

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