Ammonia → HCID 178464433, compound

HRID 614690Notes

Reaction equation

HRID 614690 reaction equation
[Cl-].[CH2:2]([N:4]([C:8]1[CH:13]=[CH:12][C:11]([N+:14]#[N:15])=[CH:10][CH:9]=1)[CH2:5][CH2:6][OH:7])[CH3:3].N([O-])=O.[Na+].Cl.[CH:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[C:23]([OH:31])[C:22]=1[OH:32].[NH3:33]>N1C=CC=CC=1.O>[CH2:2]([N:4]([C:8]1[CH:13]=[CH:12][C:11]([N:14]=[N:15][C:24]2[C:25]3[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:21]([N:33]=[N:14][C:11]3[CH:10]=[CH:9][C:8]([N:4]([CH2:5][CH2:6][OH:7])[CH2:2][CH3:3])=[CH:13][CH:12]=3)=[C:22]([OH:32])[C:23]=2[OH:31])=[CH:10][CH:9]=1)[CH2:5][CH2:6][OH:7])[CH3:3]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 70912,3-DihydroxynaphthaleneHCID 67259Benzenediazonium, 4-[ethyl(2-hydroxyethyl)amino]-, chloride (1:1)HCID 23668193Sodium Nitrite

Product 1

HCID 178464433HCID 178464433, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A solution of 0.200 mole of p-(N-ethyl-N-2-hydroxyethylamino)benzenediazonium chloride (made as in the preceding procedure using twice the amount of PDA, sodium nitrite, hydrochloric acid and water) was added dropwise with stirring at 0°-5° C. to a solution of 15.9 g. (0.0994 mole) of 2,3-naphthalenediol, 400 ml. of pyridine and 150 ml. of aqueous 28% ammonia. The mixture was stirred for 11/2 hr. after completion of the addition. The solid was collected, washed with methanol and then water, and dried in vacuum at 45° C. to give 42.3 g. of green product, m.p. 240° C. Recrystallization from 400 ml. of pyridine gave 33.2 g. (61.6%) of green crystals, m.p. 247° C. (dec.),

Workup

  1. additionwas added dropwise
  2. stirringThe mixture was stirred for 11/2 hr
  3. additionafter completion of the addition
  4. customThe solid was collected
  5. washwashed with methanol
  6. dry with materialwater, and dried in vacuum at 45° C.
  7. customto give 42.3 g
  8. customRecrystallization from 400 ml
  9. customof pyridine gave 33.2 g

Sources & evidence

ORD record
ord-d0772f77e79843a29730dbffee795c54
Source dataset
uspto-grants-1979_03
Patent number
US04145299

Reaction notes

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